lecture 27.3

lecture 27.3 - 27-27-1Organic Organic H BrownWilliam H...

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Unformatted text preview: 27-27-1Organic Organic ChemistryChemistryWilliam H. BrownWilliam H. BrownChristopher S. FooteChristopher S. FooteBrent L. IversonBrent L. Iverson27-27-2Amino AcidsAmino Acids& Proteins& ProteinsChapter 27Chapter 2727-27-3Solid-Phase SynthesisSolid-Phase Synthesis◆Bruce Merrifield, 1984 Nobel Prize for Chemistry•solid support: a type of polystyrene in which about 5% of the phenyl groups carry a -CH2Cl group•the amino-protected C-terminal amino acid is bonded as a benzyl ester to the support beads•the polypeptide chain is then extended one amino acid at a time from the N-terminal end•when synthesis is completed, the polypeptide is released from the support beads by cleavage of the benzyl ester27-27-4Solid-Phase SynthesisSolid-Phase Synthesis◆Figure 27.10 The solid support used in the Merrifield solid phase synthesis27-27-5Peptide Bond GeometryPeptide Bond Geometry•the four atoms of a peptide bond and the two alpha carbons joined to it lie in a plane with bond angles of 120° about C and N•the model of Gly-Gly is viewed from two perspectives to show the planarity of the six atoms of the peptide bond27-27-6Peptide Bond GeometryPeptide Bond Geometry•to account for this geometry, Linus Pauling proposed that a peptide bond is most accurately represented as a hybrid of two contributing structures•the hybrid has considerable C-N double bond character and rotation about the peptide bond is restrictedCαΧαΝΗΧΧαΧαΟΟΧΝΗ+-27-...
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lecture 27.3 - 27-27-1Organic Organic H BrownWilliam H...

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