© 2013MIT Structure-Function-Properties: Chirality Structure-Function-Properties Series Structure-Function-Properties Developed by the bythe Developed Teaching and Learning Laboratory at MIT for the Singapore University of for Singapore the University Technology and Design Introduction Additional Resources 304Materials Soph Learning Objectives Learning toUse this Video When References Going Further Post-Video Materials Pre-Video Materials Summary Video Highlights Video Information Key Experience Student Motivation Instructor’s Guide . Chirality Table ofContents ...... Page 1 Page . . . . 2 2 6 6 6 5 4 4 3 3 2 2 2 2

+

Resources Soph 304 Intro ContentsContents © 2013MIT Structure-Function-Properties: Chirality thevideo,During studentswill: activities theirsolutions onagainstthevideo theirown andthencheck recommendedIt ishighly thatthevideoispausedwhenprompted sothatstudentsare abletoattemptthe Experience Student rolefunction andproperties inbiological acrucial plays understanding ofhow chirality moleculeanditsmirrora chiral image compound are notthesamemolecule Perhaps needed, skills duetothe3Dvisualization many studentshave ahard timeunderstandingthat Motivation beableto: thisvideostudentswill watching After Objectives Learning toUse this When Video Introduction • • • • • • • • its three-dimensional structure acids, anunderstandingofwhataprotein isand amino occurring ofthe20naturally structure Prior knowledge: Moleculargeometry, the 304,In Soph orinrecitation, inclass after Examine the primary and secondary structure of the anti-freeze protein, ofthe anti-freeze structure ofits and secondary thesymmetry Examine the primary oftheobjectmakes whatproperty todetermine Identify objectsthatareandtry notchiral binding partner, water, andhow thesetwo moleculesbind presented basedon inthevideo rules whetheramoleculeischiral Determine it achiral objectsthatarechiral everyday Think of arole plays compounds inthefunction of biological Understand how chirality objectsandmolecules Identify chiral 3:Lecture Proteins .

. Page 2 Page . . (optional) • Materials Needed: Narrator: Prof Duration: 13:48 Information Key

molecular .

. . Students will gainan will Students

modeling . BradP .

set entelute .

.

Resources Soph 304 IntroIntro Contents © 2013MIT Structure-Function-Properties: Chirality ideasfromThis tableoutlinesacollectionof activities andimportant thevideo Highlights Video 10:07 8:33 5:35 4:07 1:25 Time proteins are discussed, proteins antifreeze specifically are orachiral chiral andfunctionmolecular structure In thisvideo, studentsare introduced moleculesandtherelationship totheconcept of chiral between Summary Video temperatures by bindingtowater in organismsthatlive insub-freezing proteinThe anti-freeze stopsicegrowth proteinThe anti-freeze isintroduced introduced innatureorganic moleculesfound asaminoacids,such drugs, andother compounds biological Examples include moleculesareChiral introduced this relates toobjectsthatare notchiral life objects from everyday Mirror-image proteins (D-proteins) are andhow that have aplaneofsymmetry are askedtothinkofobjects Students are shownStudents examplesofchiral Feature . Students then extend this idea to small moleculesandpr thenextendthisideatosmall Students . . Students firstanaly Students . .

.

. .

Page 3 Page . image proteins, intothemirror fold image oftheir acids proteins made ofD-amino entirely synthesize acids only In nature, from proteins areL-amino synthesized are not to show why some objectsarewhileothers chiral isintroduced The concept ofaplane symmetry conceptyour for be anew students isintroduced chirality of The property acids from D-amino all synthesized to bechemically proteinThe anti-freeze is one ofthefirst proteins L-protein occurring counter-part naturally Comments . ze some everyday objects and determine if they ifthey objectsanddetermine some everyday ze . . These proteins, mirror arecalled which

.

. Scientists can no can Scientists . oteins w chemically w chemically . Mirror image . . This may .

Resources Soph 304 IntroIntro Contents © 2013MIT Structure-Function-Properties: Chirality activitiesfollowing anddiscussions appropriate,When ofsome ofthe thisguideisaccompanied by additionaltoaidinthedelivery materials Materials Pre-Video 304Materials Soph

following moleculesorionsfollowing 1. Have students examine the four levels ofproteinHave levels students examinethefour structure usingfreestructure tools, visualization ( asStarBiochem such ( bediscussedinthevideo will Have your protein, studentslook ofthesnow atthestructure fleaanti-freeze 3. aprotein that groups, acidic groups andbasicgroups 20 aminoacids?acidhave Identifywhich sidechains non-polar groups, polarneutral features arefunctional groups common 20aminoacids?are toall present What What inthe 2. (g) NH )H (f (c) H (b) CO (a) CH (e) CH (d) H http://www Work atom(s) aboutthecentral ofeach topredict thegeometry withapartner 2 2 2 O O CO 4 3 2 2 + 2 CH 3 . rcsb . org/pdb/home/home .

. Amolecularmodelingkitmay beuseful . The proteincanbedo . . do Page 4 Page ), pdbID: 3BOI wnloaded from theProtein DataBank .

. Students can view thepr view can Students http://star .

. mit . edu/biochem otein /) .

Resources SophSoph 304 Intro Contents © 2013MIT Structure-Function-Properties: Chirality Post-Video Materials

the natural proteinthe natural Themirror image protein ofthesnow 2. fleaantifreeze protein bindswaterinthesame way as sodifferently smell the enantiomers ofcarvone plastic bags insmall andpassthesearound theclass seedstoclass leaves spearmint andcaraway Bring 1. proteins that bind with the same binding partner as their natural protein astheirnatural proteins counterpart thatbindwiththesamebindingpartner . giv This will . . Discuss the possible implications ofbeingabletosy Discussthepossibleimplications e the students the chance to smell two different tosmell odorscominge thestudentschance from . Have your studentsdiscusswh Page 5 Page y these seemingly similarmolecules y theseseemingly nthesize mirror imagenthesize .

Resources SophSoph 304 Intro Contents © 2013MIT Structure-Function-Properties: Chirality containsaboutthesnow information fleaantifreeze protein: following article The were resources articles inthedevelopment ofthisvideo: following journal The textbooks covered by isgenerally mostorganicchemistry Chirality References example,for ofmoleculesanddiastereomers byintotherelatedactivity topicsofoptical delving This videoprovided anintroduction totheconceptchirality of Going Further Additional Resources • • • • • Determined by Racemic Crystallization of Synthetic Protein ofSynthetic Enantiomers byDetermined Crystallization Racemic A Pentelute, B 598-603 Courses UndergraduateChemistry Examples for Kraft, P Education Chemical of Journal Moleculeswith ofChiral Non-superimposability Models toShow Their Mirror Images Collins, M Bruice, P Straumanis, A American Chemical Society Chemical American . A . , andKent, B Stephen . andMannschrec . .

(2007) . J . L . andEasdon, J . (2009) . , Gates, .

Organic Chemistry. .

Z Organic Chemistry . k, A , 130(30), 9695-9701 P . . . H (2001) , , 78(11), 1484-1485 Tereshko, V . (2010) . (2008) . Page 6 Page DemonstratingChir Upper Saddle River: Prentice UpperSaddle Hall . ofOdorS The Enantioselectivity . X-rayS . . , Dashnau, Boston: Houghton MifflinHarcourt . . tructure of Snow Flea Antifreeze Protein Antifreeze Flea ofSnow tructure You ma . .

, Education Chemical of Journal 87(6), J .

. L . y wishtoexaminethisarea further, , ality: Using a Mirror with Physical Using aMirrorality: withPhysical Vanderkrooi, J . ensation: Some . M .

Journal of the of Journal . , Kossiakoff . . .

,

ResourcesResources Soph 304 Intro Contents MIT OpenCourseWare http://ocw.mit.edu

RES.TLL.004 STEM Concept Videos Fall 2013

For information about citing these materials or our Terms of Use, visit: http://ocw.mit.edu/terms.