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A Dde resin based strategy for inverse solid‐phase synthesis of amino terminated peptides, peptide mimetics and protected peptide intermediates
Author(s) -
Rai Aman,
Gutheil William G.
Publication year - 2005
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/psc.594
Subject(s) - peptide , peptide synthesis , chemistry , epimer , protecting group , combinatorial chemistry , amino acid , yield (engineering) , solid phase synthesis , side chain , stereochemistry , organic chemistry , biochemistry , alkyl , materials science , metallurgy , polymer
This report describes a Dde resin based attachment strategy for inverse solid‐phase peptide synthesis (ISPPS). This attachment strategy can be used for the synthesis of amino terminated peptides with side chains and the carboxyl terminus either protected or deprotected. Amino acid t ‐butyl esters were attached through their free amino group to the Dde resin. The t ‐butyl carboxyl protecting group was removed by 50% TFA, and inverse peptide synthesis cycles performed using an HATU/TMP based coupling method. Protected peptides were cleaved from the resin with dilute hydrazine. Side chain protecting groups could then be removed by treatment with TFMSA/TFA. The potential of this approach was demonstrated by the synthesis of several short protected and unprotected peptides in good yield and with low epimerization. Its potential for peptide mimetic synthesis was demonstrated by the synthesis of two peptide trifluoromethylketones. Copyright © 2004 European Peptide Society and John Wiley & Sons, Ltd.