Fmoc-Protected trans-4-Methylproline
Introduction
Substituted prolines are considered to be analogues of natural amino acids, and their incorporation into peptides serves a couple purposes.
- Superior pharmaceutical agents
- Establishing structure, aiding in further understanding of biological processes
Syntheses of 3- and 5-substituted prolines has been accomplished to date, however there have been very few syntheses of 4-substituted prolines.
The couple procedures for the latter have given poor results for the synthesis of only a trans diastereomer:
- Conversion from glutamic acid leading to a 2:1 ratio trans:cis
- Synthesis from 4-hydroxyproline by tosyl formation leading to a 2:3 ratio trans:cis
- Friedel-Crafts reactions of benzene with different trans-4-hydroxyproline derivatives gave a little better results
Their objective was to synthesize a trans-4-methylproline in a better diastereomeric ratio then the previous studies and take from that
pathway a universal synthesis for future 4-alkylprolines.
Goto The Synthesis Overview
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Kevin Bruce