Solid Phase Peptide Synthesis
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1 Solid Phase Peptide Synthesis Fischer Projections revisited C C C Remember that group rotations are always allowed C C 80 rotations of entire molecule are allowed C 80 C 90 rotations of entire molecule are NT allowed C 90 x C C C C C C x C
2 mirror images are enantiomers C C C C identification of compounds by a horizontal mirror plane MES compounds C C C C C mirror plane C
3 a elpful way to assign stereochemistry C C C lowest priority group on bottom notice that lowest priority group () is in the back C C lowest priority group on side C notice that lowest priority group () is in the front If the lowest priority group is on the top or bottom: assign 'as normal' C clockwise = R F counterclockwise = S BUT If the lowest priority group is on the SIDE: make the PPSITE ASSIGNMENT C clockwise = S (opposite of the 'normal assignment) C F counterclockwise = R (opposite of the 'normal assignment) C C not a stereocenter
4 Carbohydrates: C n n C C all of the natural sugars have R configuration at this stereocenter. D-glucose: an aldohexose aldehyde sugar six carbon Dextrorotatory = D configuration for sugars Levorotatory = L -configuration for sugars C C D-fructose: a ketohexose C C D-ribose: an aldopentose pen chain sugars can equilibrate with cyclic hemiacetals Cyclic hemiacetal formation mech glucose C C K, so this is how they drew it back in the 800 s
5 aworth Projections For glucose C C C + 90 turn anomer + " anomer For ribose C C 90 turn C squiggly line represents mixture of and " anomers Converting aworth Projections to Chair Projections For glucose 6 anomer 6 equatorial 6 anomer 6 axial Mutarotation of glucose cat + or D = + D = +
6 ligosaccharides and Polysaccharides a disaccharide cellulose : a glucose polymer etc maltose (beer): a glucose dimer highly linear strucrture: very effective for intrastrand -bonding insoluble: cell walls starch: two components amylose (~0%) soluble starch amylopectin (~80%) insoluble starch ligosaccharides and Polysaccharides Amylose is highly helical end view amylose
7 Some reactions of sugars Kiliani Fischer Synthesis separable C C arabinose an aldopentose ) NaCN ) /Pd BaS ) + C C glucose an aldohexose + C C Mannose an aldohexose NaCN + N C C a cyanohydrin /Pd BaS C N C Intermediate from reduction step Some reactions of sugars Wohl Degradation C C glucose an aldohexose N- N C Ac ) N- ) Ac ; NaMe ) + Ac Ac N Ac Ac Ac Ac C Ac C C arabinose an aldopentose Ac N Ac Ac Ac C Ac + (retro cyanohydrin) NaMe + N C
8 xidation of sugars C N C C C glucose C C N C C mirror plane xylose optically inactive The Fischer Proof
9 The Fischer Proof N N N N C C C C C C C C The Fischer Proof C C N N C C N N N N C C C C C C C C
10 The Fischer Proof It is arabinose C C N N C C N N N N C C C C C C C C The Fischer Proof: Fischer used this type of analysis for all of the Sugars, starting from a good guess for glyceraldehyde It is arabinose C C N N C C N N N N C C C C C C C C
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