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<title>DP Chemistry: Taxol - a chiral auxiliary case study</title>
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<meta name="description" content="Paclitaxel, (which has the trade name of Taxol) is an incredibly complex molecule with no fewer than eleven chiral centres. It is possible to get side-tracked into some very complicated chemistry when teaching this topic so it helps to keep clear in your mind exactly what this topic is covering. The following checklist may help.1. Natural source of taxolTaxol is an effective chemotherapeutic agent that occurs naturally,...">
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</a></li><li><a href="../19287/proteins-enzymes--1.html">Proteins & enzymes </a></li><li><a href="../19291/lipids-1.html">Lipids</a></li><li><a href="../19299/carbohydrates--1.html">Carbohydrates </a></li><li><a href="../19305/vitamins--1.html">Vitamins </a></li><li><a href="../19313/biochemistry-the-environment--1.html">Biochemistry & the environment </a></li><li><a href="../19336/proteins-enzymes-ahl--1.html">Proteins & enzymes (AHL) </a></li><li><a href="../19347/nucleic-acids--1.html">Nucleic acids </a></li><li><a href="../19361/biological-pigments--1.html">Biological pigments </a></li><li><a href="../19366/stereochemistry-in-biomolecules-1.html">Stereochemistry in biomolecules</a></li></ul></li><li><a href="../19390/option-c--1.html" class="father">Option C </a><ul class="level-2"><li><a href="../19391/energy-sources-1.html">Energy sources</a></li><li><a href="../19407/fossil-fuels-1.html">Fossil fuels</a></li><li><a href="../19411/nuclear-fusion-nuclear-fission-reactions-1.html">Nuclear fusion & nuclear fission reactions</a></li><li><a href="../19429/solar-energy-1.html">Solar energy</a></li><li><a href="../19437/environmental-impact-global-warming-1.html">Environmental impact - global warming</a></li><li><a href="../19453/electrochemistry-rechargeable-batteries-fuel-cells-1.html">Electrochemistry, rechargeable batteries & fuel cells</a></li><li><a href="../19458/nuclear-fusion-fission-hl--1.html">Nuclear fusion & fission (HL) </a></li><li><a href="../19470/photovoltaic-cells-and-dsscs-1.html">Photovoltaic cells and DSSCs</a></li></ul></li><li class="selected"><a href="../19078/option-d-1.html" class="father">Option D</a><ul class="level-2"><li><a href="../19079/pharmaceutical-products-drug-action--1.html">Pharmaceutical products & drug action </a></li><li><a href="../19158/aspirin-penicillin--1.html">Aspirin & penicillin </a></li><li><a href="../19174/opiates-1.html">Opiates</a></li><li><a href="../19184/ph-regulation-of-the-stomach-1.html">pH regulation of the stomach</a></li><li><a href="../19194/antiviral-medications--1.html">Antiviral medications </a></li><li><a href="../19211/environmental-impact-of-some-medications-1.html">Environmental impact of some medications</a></li><li class="selected"><a href="taxol-a-chiral-auxiliary-case-study-1.html">Taxol - a chiral auxiliary case study</a></li><li><a href="../19258/nuclear-medicine--1.html">Nuclear medicine </a></li><li><a href="../19273/drug-detection-analysis--1.html">Drug detection & analysis </a></li></ul></li></ul></li><li><a href="../16592/practical-scheme-of-work-ia--1.html">Practical scheme of work & IA </a><ul class="level-1"><li><a href="../16682/internal-assessment-1.html" class="father">Internal Assessment</a><ul class="level-2"><li><a href="../18892/scaffolding-the-investigation-1.html">'Scaffolding' the investigation</a></li><li><a href="../18896/timing-organisation--1.html">Timing & organisation </a></li><li><a href="../18905/choosing-the-research-question-1.html">Choosing the research question</a></li><li><a href="../18946/personal-engagement-1.html">Personal engagement</a></li><li><a href="../18950/exploration-1.html">Exploration</a></li><li><a href="../18957/analysis-1.html">Analysis</a></li><li><a href="../18965/evaluation-1.html">Evaluation</a></li><li><a href="../18966/communication-1.html">Communication</a></li><li><a href="../19882/internal-standardization-of-the-ia-1.html">Internal standardization of the IA</a></li><li><a href="../19901/submitting-the-samples-for-moderation-2.html">Submitting the samples for moderation</a></li><li><a href="../33754/ten-suggestions-for-ias-using-secondary-data-1.html">Ten suggestions for IAs using secondary data</a></li><li><a href="../37544/gaining-full-marks-for-a-databased-ia--1.html">Gaining full marks for a databased IA </a></li><li><a href="../19506/ia-example-marking-exercise--1.html">IA example & marking exercise </a></li><li><a href="../23929/genuine-examples-of-moderated-ia-reports-1.html">Genuine examples of moderated IA reports</a></li><li><a href="../25234/examples-of-teacher-marked-ia-reports--1.html">Examples of teacher-marked IA reports </a></li><li><a href="../37542/history-of-internal-assessment-1.html">History of Internal Assessment</a></li></ul></li><li><a href="../16598/mandatory-laboratory-components-1.html" class="father">Mandatory laboratory components</a><ul class="level-2"><li><a href="../16613/formula-of-magnesium-oxide--1.html">Formula of magnesium oxide </a></li><li><a href="../16612/determining-the-mr-of-an-unknown-gas-1.html">Determining the <i>M</i><sub>r</sub> of an unknown gas</a></li><li><a href="../16615/acid-base-titrations--1.html">Acid-base titrations </a></li><li><a href="../16616/a-green-acid-base-practical-1.html">A green acid-base practical</a></li><li><a href="../16617/analysis-of-aspirin-tablets-1.html">Analysis of aspirin tablets</a></li><li><a href="../16618/caco3-in-egg-shells-1.html">CaCO<sub>3</sub> in egg shells</a></li><li><a href="../16644/enthalpy-changes-1.html">Enthalpy changes</a></li><li><a href="../16631/reaction-rates-1.html">Reaction rates</a></li><li><a href="../16635/rate-dependent-factors-1.html">Rate-dependent factors</a></li><li><a href="../16636/determining-ea-for-a-reaction-1.html">Determining <i>E</i><sub>a</sub> for a reaction</a></li><li><a href="../16637/iodination-of-propanone-1.html">Iodination of propanone</a></li><li><a href="../18144/titrations-with-a-ph-meter-1.html">Titrations with a pH meter</a></li><li><a href="../18355/redox-titration-with-kmno4--1.html">Redox titration with KMnO<sub>4</sub> </a></li><li><a href="../16640/voltaic-cells-1.html">Voltaic cells</a></li><li><a href="../16659/3-d-molecular-modelling--1.html">3-D molecular modelling </a></li></ul></li><li><a href="../17168/other-good-practicals-1.html" class="father">Other good practicals</a><ul class="level-2"><li><a href="../17196/common-chemical-reactions-1.html">Common chemical reactions</a></li><li><a href="../227/elements-oxides-of-the-third-period--1.html">Elements & oxides of the third period </a></li><li><a href="../17239/the-halogens-1.html">The halogens</a></li><li><a href="../17162/boiling-points-of-mixtures-1.html">Boiling points of mixtures</a></li><li><a href="../17170/polarity-of-molecules-1.html">Polarity of molecules</a></li><li><a href="../18083/le-chateliers-principle--1.html">Le Chatelier's principle </a></li><li><a href="../19582/determining-kc-for-an-esterification-reaction-1.html">Determining <i>K</i><sub>c</sub> for an esterification reaction</a></li><li><a href="../18164/redox-reactions-of-vanadium--1.html">Redox reactions of vanadium </a></li><li><a href="../18351/chlorine-in-swimming-pools--1.html">Chlorine in swimming pools </a></li><li><a href="../18178/analysis-of-cuii-ions-in-solution--1.html">Analysis of Cu(II) ions in solution </a></li><li><a href="../18179/percentage-of-copper-in-brass-1.html">Percentage of copper in brass</a></li><li><a href="../18356/electrolytic-cells--1.html">Electrolytic cells </a></li><li><a href="../18598/reactions-of-organic-compounds-1.html">Reactions of organic compounds</a></li><li><a href="../18752/hydrolysis-of-halogenoalkanes-1.html">Hydrolysis of halogenoalkanes</a></li><li><a href="../18784/preparation-of-13-dinitrobenzene--1.html">Preparation of 1,3-dinitrobenzene </a></li><li><a href="../19022/determination-of-an-organic-structure-1.html">Determination of an organic structure</a></li><li><a href="../19887/preparation-of-nylon-66-1.html">Preparation of nylon 6,6</a></li><li><a href="../19343/determination-of-vitamin-c-content--1.html">Determination of vitamin C content </a></li><li><a href="../19342/hydrolysis-of-starch--1.html">Hydrolysis of starch </a></li><li><a href="../19159/preparation-purification-of-aspirin--1.html">Preparation & purification of aspirin </a></li></ul></li><li><a href="../18851/ict-in-practical-work-1.html" class="father">ICT in practical work</a><ul class="level-2"><li><a href="../18852/data-logging--1.html">Data logging </a></li><li><a href="../18853/software-for-graph-plotting--1.html">Software for graph plotting </a></li><li><a href="../18854/spreadsheets-for-data-processing--1.html">Spreadsheets for data processing </a></li><li><a href="../18855/databases-1.html">Databases</a></li><li><a href="../18856/computer-modelling-simulations--1.html">Computer modelling & simulations </a></li></ul></li><li><a href="../16594/group-4-project-1.html" class="father">Group 4 Project</a><ul class="level-2"><li><a href="../16595/practicalities-1.html">Practicalities</a></li><li><a href="../16596/reflective-statement--2.html">Reflective statement </a></li></ul></li><li><a href="../16666/a-new-laboratory-1.html">A new laboratory?</a></li></ul></li><li><a href="../16284/exams-1.html">Exams</a><ul class="level-1"><li><a href="../16286/essential-facts-1.html" class="father">Essential Facts</a><ul class="level-2"><li><a href="../16287/objectives-command-terms-1.html">Objectives & command terms</a></li><li><a href="../16288/grade-descriptors-1.html">Grade descriptors</a></li><li><a href="../16289/grade-boundaries-1.html">Grade boundaries</a></li></ul></li><li><a href="../16302/paper-1-multiple-choice-1.html" class="father">Paper 1 (Multiple Choice)</a><ul class="level-2"><li><a href="../16303/advice-to-students-paper-1-1.html">Advice to students (Paper 1)</a></li><li><a href="../31515/practice-paper-1-exams-1.html">Practice Paper 1 exams</a></li></ul></li><li><a href="../16305/paper-2-1.html" class="father">Paper 2</a><ul class="level-2"><li><a href="../16306/advice-to-students-paper-2-1.html">Advice to students (Paper 2)</a></li><li><a href="../16307/areas-of-difficulty-1.html">Areas of difficulty</a></li></ul></li><li><a href="../16313/paper-3--1.html" class="father">Paper 3 </a><ul class="level-2"><li><a 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href="../16323/retaking-the-exam-1.html">Retaking the exam</a></li></ul></li><li><a href="../16325/faqs-1.html">FAQs</a></li></ul></li><li><a href="../3147/ib-core-1.html">IB Core</a><ul class="level-1"><li><a href="../3149/learner-profile-1.html">Learner Profile</a></li><li><a href="../21735/extended-essays--1.html" class="father">Extended Essays </a><ul class="level-2"><li><a href="../21736/overview--1.html">Overview </a></li><li><a href="../21780/responsibilities-1.html">Responsibilities</a></li><li><a href="../21790/resources-1.html">Resources</a></li><li><a href="../21800/research-1.html">Research</a></li><li><a href="../21804/writing-the-essay-1.html">Writing the essay</a></li><li><a href="../21810/assessment-1.html">Assessment</a></li><li><a href="../22434/summary-of-advice--1.html">Summary of advice </a></li><li><a href="../25272/faqs--1.html">FAQs </a></li></ul></li><li><a href="../307/theory-of-knowledge-tok-1.html" class="father">Theory of Knowledge (TOK)</a><ul class="level-2"><li><a href="../41171/the-12-tok-concepts-1.html">The 12 TOK concepts</a></li><li><a href="../3507/why-tok-chemistry-1.html">Why TOK & Chemistry?</a></li><li><a href="../3505/a-modern-paradigm-1.html">A modern paradigm</a></li></ul></li></ul></li><li><a href="../17783/fast-track-to-tests-questions-1.html">Fast track to tests & questions</a><ul class="level-1"><li><a href="../17784/sl-multiple-choice-tests-on-individual-topics-1.html">SL Multiple choice tests on individual topics</a></li><li><a href="../24351/sl-multiple-choice-quizzes-on-sub-topics-1.html">SL Multiple choice 'quizzes' on sub-topics</a></li><li><a href="../31519/sl-practice-paper-1-exams-1.html">SL Practice Paper 1 exams</a></li><li><a href="../17786/sl-questions-on-each-sub-topic-1.html">SL Questions on each sub-topic</a></li><li><a href="../20431/sl-paper-3-section-a-questions-1.html">SL Paper 3 Section A questions</a></li><li><a href="../17792/sl-questions-on-the-options-1.html">SL Questions on the options</a></li><li><a href="../24897/sl-quizzes-on-option-sub-topics--1.html">SL Quizzes on option sub-topics </a></li><li><a href="../17785/hl-multiple-choice-tests-on-individual-topics-1.html">HL Multiple choice tests on individual topics</a></li><li><a href="../24352/hl-multiple-choice-quizzes-on-sub-topics-1.html">HL Multiple choice 'quizzes' on sub-topics</a></li><li><a href="../31520/hl-practice-paper-1-exams--1.html">HL Practice Paper 1 exams </a></li><li><a href="../17787/hl-questions-on-each-sub-topic--1.html">HL Questions on each sub-topic </a></li><li><a href="../20428/hl-paper-3-section-a-questions-1.html">HL Paper 3 Section A questions</a></li><li><a href="../17793/hl-questions-on-the-options-1.html">HL Questions on the options</a></li><li><a href="../24973/hl-quizzes-on-option-sub-topics-1.html">HL Quizzes on option sub-topics</a></li><li><a href="../41573/printable-versions-of-written-tasks--1.html">Printable versions of written tasks </a></li></ul></li><li><a 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biomolecules</a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../25034/mc-test-stereochemistry-in-biomolecules--1.html" title="MC test: Stereochemistry in biomolecules ">MC test: Stereochemistry in biomolecules </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../19373/stereochemistry-in-biomolecules-questions-1.html" title="Stereochemistry in biomolecules questions">Stereochemistry in biomolecules questions</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../24871/stereochemistry-in-biomolecules-answers--1.html" title="Stereochemistry in biomolecules answers ">Stereochemistry in biomolecules answers </a></li></ul></ul><li class=" parent" style="padding-left: 0px"><i class="expander fa fa-caret-right "></i><a href="../19390/option-c--1.html" title="Option C ">Option C </a></li><ul class="level-1 "><li class=" 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</div><section id="main-content"><div id="toc-1672969711" class="toc"><a href="#" class="toc-switcher" title="Show table of contents"><small><i class="fa fa-reorder"></i> Table of contents <span class="pull-right"><i class="fa fa-chevron-down"></i></span></small></a></div><h1><img class="ico" src="../../../img/icons/higher-1.png"> D.7 Taxol - a chiral auxiliary case study (2 hours)</h1><div class="pinkBg"><div><h2>Pause for thought</h2><p>Paclitaxel, (which has the trade name of Taxol) is an incredibly complex molecule with no fewer than eleven chiral centres. It is possible to get side-tracked into some very complicated chemistry when teaching this topic so it helps to keep clear in your mind exactly what this topic is covering. The following checklist may help.</p><p style="margin-left:36.0pt;"><strong>1.</strong> <strong>Natural source of taxol</strong><br>Taxol is an effective chemotherapeutic agent that occurs naturally, mainly in the Pacific yew tree, but only in very small amounts. Even if this tree is grown commercially it cannot produce all the taxol required for therapeutic use.</p><p style="margin-left:36.0pt;"><strong>2. Structure of taxol</strong><br>A molecule of taxol contains 11 chiral centres.</p><p style="margin-left:36.0pt;"><strong>3.</strong> <strong>Chemotherapeutic properties of taxol</strong><br>It is effective against several different types of cancer (e.g. ovarian, breast, lung and pancreatic cancers). It works by interfering with tumour cell division by binding to certain proteins called tubulins.</p><p style="margin-left:36.0pt;"></p><p style="margin-left:36.0pt;"><strong>4.</strong> <strong>Semi-synthesis of taxol</strong><br>It can be semi-synthesised from Baccatin III, a precursor of taxol which is also found in yew trees.</p><p style="margin-left: 36pt; text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/Options/Option%20D/baccatin-iii-(1).png" style="width: 317px; height: 279px;"></p><p style="margin-left: 36pt; text-align: center;">Baccatin III</p><hr class="hidden"><p style="margin-left:36.0pt;">To obtain the correct stereochemical configuration in the side chains of taxol, use of chiral auxiliaries is made.</p><hr class="hidden"><p style="margin-left:36.0pt;"></p><p style="margin-left:36.0pt;"><strong>5. Chiral auxiliaries</strong><br>A chiral auxiliary is a specific enantiomer of a reagent, which can be attached to the starting material to create the stereochemical conditions necessary for only the desired enantiomeric product to be formed. After the product has been formed the chiral auxiliary is removed and recycled.</p><p style="margin-left: 36pt; text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/2014-Options/Option-D/2-phenylcyclohexanol(1S2R).jpg" style="width: 252px; height: 209px;"></p><p style="margin-left: 36pt; text-align: center;"><em>trans</em>-2-phenylcyclohexan-1-ol - a chiral auxiliary used in the synthesis of taxol</p><hr class="hidden"><p style="margin-left:36.0pt;"></p><p style="margin-left:36.0pt;"><strong>6.</strong> <strong>Test for purity using a polarimeter</strong><br>A pure enantiomer will rotate the plane of plane-polarized light either clockwise or anti-clockwise by a fixed number of degrees. By using a polarimeter and measuring the angle of rotation the percentage purity of the desired enantiomer in the product can be determined.</p><hr class="hidden"></div></div><hr class="hidden"><div class="box"><h2>Nature of Science</h2><p>The demand for certain drugs is greater than the supply of natural substances required to synthesize them. However, due to advances in technology, many natural substances can now be produced in laboratories in large enough amounts to meet the demand.</p><hr class="hidden"></div><hr class="hidden"><div class="box"><table align="left" border="0" cellpadding="10" cellspacing="0"><tbody><tr><td style="width: 50%;" valign="top"><div class="yellowBg"><div><h2>Learning outcomes</h2><p>After studying this topic students should be able to:</p><p><strong>Understand:</strong></p><ul><li>Taxol is a medicament that is commonly used to treat several different forms of cancer.</li><li>Taxol occurs naturally in certain types of yew tree but it is now commonly produced synthetically.</li><li>Chiral auxiliaries are optically active substances that are incorporated temporarily into organic syntheses so that they can be carried out asymmetrically to selectively produce a single enantiomer.<hr class="hidden"></li></ul><p><strong>Apply their knowledge to:</strong></p><ul><li>Explain how paclitaxel (Taxol is the trademark name) is obtained and used as a chemotherapeutic agent.</li><li>Describe the use of chiral auxiliaries to form the desired enantiomeric product.</li><li>Explain how a polarimeter can be used to identify enantiomers.</li></ul></div></div></td><td style="width: 50%;" valign="top"><h4><b><span style="font-weight: normal;"></span></b></h4><div class="yellowBg"><div><h4><b><span style="font-weight: normal;"><strong>Clarification notes</strong></span></b></h4><p>The structure of Taxol (paclitaxel) is given in Section 37 of the data booklet.</p><hr class="hidden"><h4 id="anchor-5">International-mindedness</h4><p>The availability and distribution of certain medicines and drugs around the world is unequal.</p></div></div></td></tr></tbody></table></div><hr class="hidden"><div class="box"><table align="left" border="0" cellpadding="10" cellspacing="0"><tbody><tr><td style="width: 50%;" valign="top"><h2><span style=""><b><span style="font-weight: normal;"><strong>Teaching tips</strong></span></b></span></h2><p>What is important when teaching this topic is to try to emphasise the principles underlying it without getting too involved in the complex chemistry of taxol. It might be worth asking students to do their own research on the history of taxol and why it is such an important chemotherapy drug and how it functions in the body against cancerous cells. Stress both the environmental and economic problems of relying on one particular natural resource and why the synthesis of taxol is such a difficult task.</p><p>Use taxol to reinforce the concept of optical isomerism and ensure your students can identify chiral carbon atoms within a molecule using skeletal structures as well as full 3-D structures. The use of molecular modelling kits is extremely useful here. They should also be able identify the important functional groups in taxol and its precursor. Explain how chiral auxiliaries work and stress that without them the amount of desired product is much lower as racemic mixtures will be formed. It is then very difficult to separate the desired enantiomer from the mixture resulting in very low yields. It is probably worth using, or repeating, <a href="../19079/pharmaceutical-products-drug-action--1.html">the thalidomide example</a> here to explain why the medication given must contain the therapeutic enantiomer and not others that may cause harm.</p><p>They will already have come across a polarimeter to distinguish between the two enantiomeric forms of an optically active compound in <a href="../18844/stereoisomerism--1.html">sub-topic 20.3 : stereoisomerism.</a> This case study goes slightly further as a calibration graph can be made of known composition against the degree of rotation of plane-polarised light. Once the degree of rotation of the final product is measured the percentage purity can be obtained by interpolation.</p><hr class="hidden"></td><td style="width: 50%;" valign="top"><h4><b><span style="font-weight: normal;"><strong>Study guide</strong></span></b></h4><p style="margin: 0px 0px 1em; padding: 0px; color: rgb(0, 0, 0); font-size: 1em;"><img alt="" src="../../../ib/chemistry/images/2014%20Basic%20information/New%20cover.jpg" style="width: 67px; height: 96px;"></p><p style="margin: 0px 0px 1em; padding: 0px; color: rgb(0, 0, 0); font-size: 1em;"></p><hr class="hidden"><p style="margin: 0px 0px 1em; padding: 0px; color: rgb(0, 0, 0); font-size: 1em;"><b><span style="font-weight: normal;">Page 1</span></b><span style="font-weight: normal;">62</span></p><p style="margin: 0px 0px 1em; padding: 0px; color: rgb(0, 0, 0); font-size: 1em;"></p><hr class="hidden"><h2>Questions</h2><p>For ten 'quiz' questions (for quick testing of knowledge and understanding with the answers explained) see <a href="../25687/mc-test-taxol-a-chiral-auxiliary-case-study-1.html" title="Options » Option D » Taxol - a chiral auxiliary case study » MC test: Taxol - a chiral auxiliary case study">MC test: Taxol - a chiral auxiliary case study</a>.</p><p>For short-answer questions see <a href="../19256/taxol-questions--1.html" title="Options » Option D » Taxol - a chiral auxiliary case study » Taxol questions ">Taxol questions </a>together with the worked answers on a separate page <a href="../25638/taxol-answers-1.html" title="Options » Option D » Taxol - a chiral auxiliary case study » Taxol answers">Taxol answers</a>.</p><hr class="hidden"><h4><span style=""><b><span style="font-weight: normal;"><strong>Vocabulary list</strong></span></b></span></h4><p><span style=""><span style="font-weight: normal;">Taxol<br>paclitaxel</span></span><br><span style=""><span style="font-weight: normal;">chiral auxiliary<br>chemotherapeutic agent</span><br><span style="font-weight: normal;">polarimeter</span></span></p></td></tr></tbody></table></div><hr class="hidden"><div class="greenBg"><div><h2 id="header-13">Teaching slides</h2><p>Teachers may wish to share these slides with students for learning or for reviewing key concepts.</p><div id="myCarousel-14" class="carousel slide" data-id="585"><!-- Carousel items --><div class="carousel-inner"><div class="active item"><a class="fancy" href="../../../tib-galleries/3-585/t1.png" rel="gallery-585" title=""><img alt="" src="files/tib-galleries/3-585/t1.png"></a><div class="carousel-caption"><p>Taxol - a chiral auxiliary case study: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-585/t2.png" rel="gallery-585" title=""><img alt="" src="files/tib-galleries/3-585/t2.png"></a><div class="carousel-caption"><p>Taxol - a chiral auxiliary case study: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-585/t3.png" rel="gallery-585" title=""><img alt="" src="files/tib-galleries/3-585/t3.png"></a><div class="carousel-caption"><p>Taxol - a chiral auxiliary case study: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-585/t4.png" rel="gallery-585" title=""><img alt="" src="files/tib-galleries/3-585/t4.png"></a><div class="carousel-caption"><p>Taxol - a chiral auxiliary case study: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-585/t51.png" rel="gallery-585" title=""><img alt="" src="files/tib-galleries/3-585/t51.png"></a><div class="carousel-caption"><p>Taxol - a chiral auxiliary case study: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-585/t6.png" rel="gallery-585" title=""><img alt="" src="files/tib-galleries/3-585/t6.png"></a><div class="carousel-caption"><p>Taxol - a chiral auxiliary case study: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-585/t7.png" rel="gallery-585" title=""><img alt="" src="files/tib-galleries/3-585/t7.png"></a><div class="carousel-caption"><p>Taxol - a chiral auxiliary case study: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-585/t8.png" rel="gallery-585" title=""><img alt="" src="files/tib-galleries/3-585/t8.png"></a><div class="carousel-caption"><p>Taxol - a chiral auxiliary case study: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-585/t9.png" rel="gallery-585" title=""><img alt="" src="files/tib-galleries/3-585/t9.png"></a><div class="carousel-caption"><p>Taxol - a chiral auxiliary case study: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-585/t10.png" rel="gallery-585" title=""><img alt="" src="files/tib-galleries/3-585/t10.png"></a><div class="carousel-caption"><p>Taxol - a chiral auxiliary case study: </p></div></div></div><!-- Carousel nav --><a class="carousel-control left" href="#myCarousel-14" data-slide="prev">‹</a><a class="carousel-control right" href="#myCarousel-14" data-slide="next">›</a><div class="tib-indicators"><img class="" title="Click to view" style="margin: 10px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-585/t1-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-585/t2-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-585/t3-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-585/t4-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-585/t51-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-585/t6-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-585/t7-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-585/t8-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-585/t9-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-585/t10-thumb128.jpg"></div></div><p> </p></div></div><hr class="hidden"><div class="blueBg"><h2><span style="font-weight: bold;">Other resources</span></h2><p><span style="font-weight: bold;">1. </span>A life science video from ScienceOnline showing that Taxol can also be obtained from Canada yew as well as Pacific yew.</p><p style="text-align: center"><iframe allowfullscreen="" frameborder="0" height="280" src="https://www.youtube.com/embed/fhGHk5mEYbw" width="360"></iframe></p><p style="text-align: center;"><a href="http://youtu.be/fhGHk5mEYbw" target="_blank" title="Videos"><img class="ico" src="../../../img/icons/video-1.png"><span class="anchor" id="video-1" name="video-1"> </span> Cancer therapy and Canada yew</a></p><hr class="hidden"><p><strong>2.</strong> Although students are not required to know in detail how Taxol works as a chemotherapeutic agent in the body it is probably good that they do have some idea. One way in which Taxol is delivered is a by binding it to albumin nanoparticles. The following video by the European Fellowship for Pharmacists explains clearly how Taxol works when bound to albumin.</p><p style="text-align: center"><iframe allowfullscreen="" frameborder="0" height="280" src="https://www.youtube.com/embed/BsLLZxXLSfA" width="360"></iframe></p><p style="text-align: center;"><a href="http://youtu.be/BsLLZxXLSfA" target="_blank" title="Videos"><img class="ico" src="../../../img/icons/video-1.png"><span class="anchor" id="video-2" name="video-2"> </span> Mechanism of action of taxol (paclitaxel</a><a href="http://youtu.be/BsLLZxXLSfA" target="_blank" title="Videos">) </a></p><hr class="hidden"><p><strong>3.</strong> A video your students might like by Richard Thornley on how chiral auxiliaries only give the desired enantiomer. It was actually made for the old programme but is still relevant to this sub-topic.</p><p style="text-align: center"><iframe allowfullscreen="" frameborder="0" height="280" src="https://www.youtube.com/embed/PbvEd_krHI8" width="360"></iframe></p><p style="text-align: center;"><a href="http://youtu.be/PbvEd_krHI8" target="_blank" title="Videos"><img class="ico" src="../../../img/icons/video-1.png"><span class="anchor" id="video-3" name="video-3"> </span> Chiral auxiliaries</a></p><hr class="hidden"><p><strong>4.</strong> A simple but effective demonstration of the principle of polarimetry.</p><p style="text-align: center"><iframe allowfullscreen="" frameborder="0" height="280" src="https://www.youtube.com/embed/3Exnt21HtPk" width="360"></iframe></p><p style="text-align: center;"><a href="http://youtu.be/3Exnt21HtPk" target="_blank" title="Videos"><img class="ico" src="../../../img/icons/video-1.png"><span class="anchor" id="video-4" name="video-4"> </span> Principle of polarimetry</a></p><hr class="hidden"><p style="text-align: center;"></p></div></section></article><section id="media-extras"><div class="page-actions no-print navbar inline hidden-desktop"><div class="navbar-inner"><ul class="nav"><li><a class="presentation" href="#" onclick="return false;"><i class="fa fa-desktop"></i></a></li><li><a class="print-section-blog" href="#" onclick="return false;"><i class="fa fa-print"></i></a></li><li><a class="page-bookmarker" data-ticket="IB Docs (2) Team" data-pid="19254" href="#" onclick="return false;"><i class="fa fa-star"></i></a></li><li><a class="personal-notes" href="#" onclick="return false;"><i class="fa fa-file-text"></i></a></li><li><a class="" data-toggle="modal" href="#modal-feedback" onclick="return false;"><i class="fa fa-envelope-o"></i></a></li><li class="dropdown"><a class="dropdown-toggle" data-toggle="dropdown" data-target="#" href="#"><i class="fa fa-share-alt"></i></a><ul class="dropdown-menu" role="menu"><li><a class="" target="_blank" title="Share on Twitter" href="https://twitter.com/share?text=%22Taxol+-+a+chiral+auxiliary+case+study%22+-+via+%40InThinker+%23chemistry%0A&url=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F19254%2Ftaxol-a-chiral-auxiliary-case-study"><i class="fa fa-twitter-square"></i><span>Twitter</span></a></li><li><a class="" target="_blank" title="Share on Facebook" href="https://www.facebook.com/sharer.php?u=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F19254%2Ftaxol-a-chiral-auxiliary-case-study&t=Taxol+-+a+chiral+auxiliary+case+study"><i class="fa fa-facebook-square"></i><span>Facebook</span></a></li><li><a class="" href="http://www.linkedin.com/shareArticle?mini=true&url=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F19254%2Ftaxol-a-chiral-auxiliary-case-study"><i class="fa fa-linkedin-square"></i><span>LinkedIn</span></a></li><li><a class="" href="https://plus.google.com/share?url=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F19254%2Ftaxol-a-chiral-auxiliary-case-study"><i class="fa fa-google-plus-square"></i><span>Google +</span></a></li><li><a class="" href="mailto:?subject=Taxol - a chiral auxiliary case study&body=Paclitaxel, (which has the trade name of Taxol) is an incredibly complex molecule with no fewer than eleven chiral centres. 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