The synthesis of 'difficult' peptides using 2-hydroxy-4-methoxybenzyl or pseudoproline amino acid building blocks: a comparative study

A comparative study has been undertaken between Hmb‐protected amino acid and pseudoproline building block analogues for use in the solid phase synthesis of ‘difficult’ peptides. Both of these derivatives act by blocking inter‐ and intramolecular hydrogen bonding, which has been shown to be a major c...

Full description

Saved in:
Bibliographic Details
Published in:Journal of peptide science 1999-09, Vol.5 (9), p.403-409
Main Authors: Sampson, Wayne R., Patsiouras, Heather, Ede, Nicholas J.
Format: Article
Language:English
Subjects:
'difficult' peptide sequences
Amino Acids - chemistry
Hmb protected amino acids
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Peptide Biosynthesis
Proline - analogs & derivatives
Proline - chemistry
pseudoproline dipeptides
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A comparative study has been undertaken between Hmb‐protected amino acid and pseudoproline building block analogues for use in the solid phase synthesis of ‘difficult’ peptides. Both of these derivatives act by blocking inter‐ and intramolecular hydrogen bonding, which has been shown to be a major cause of poor synthesis/quality/efficiency. While the two were shown to result in substantial improvements in the purity of crude peptides, pseudoproline incoporation was found to be superior to Hmb backbone protection. This was due to slow and incomplete coupling of the amino acid immediately following the Hmb amino acid. Copyright © 1999 European Peptide Society and John Wiley & Sons, Ltd.
ISSN:1075-2617
1099-1387
DOI:10.1002/(SICI)1099-1387(199909)5:9<403::AID-PSC213>3.0.CO;2-S