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The synthesis of ‘difficult’ peptides using 2‐hydroxy‐4‐methoxybenzyl or pseudoproline amino acid building blocks: a comparative study
Author(s) -
Sampson Wayne R.,
Patsiouras Heather,
Ede Nicholas J.
Publication year - 1999
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/(sici)1099-1387(199909)5:9<403::aid-psc213>3.0.co;2-s
Subject(s) - intramolecular force , amino acid , chemistry , block (permutation group theory) , hydrogen bond , combinatorial chemistry , peptide , stereochemistry , blocking (statistics) , organic chemistry , biochemistry , molecule , computer science , mathematics , computer network , geometry
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.