ORGANIC CHEM PRINT STUDY GDE & SSM
ORGANIC CHEM PRINT STUDY GDE & SSM
4th Edition
ISBN: 9781119810650
Author: Klein
Publisher: WILEY
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Chapter 25.4, Problem 25CC
Interpretation Introduction

Interpretation:

For the dipeptide Phe-Leu, s-trans conformation needs to be drawn and both N-terminus and C-terminus need to be identified.

Concept introduction:

The peptide bonds are simply amide linkages.  These amide linkages have a resonance structure where the C-N bond has got some double-bond character.  Due to this there is a restricted rotation in the amide bond as we see in normal amides.  This restricted rotation gives rise to two possible conformations known as s-trans and s-cis.

Please remember that s-trans conformation is more stable than s-cis conformation due to less steric interactions.

To draw and identify: the s-trans conformation for Phe-Leu and identify the N-terminus and C-terminus.

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Chapter 25 Solutions

ORGANIC CHEM PRINT STUDY GDE & SSM