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An unsaturated peptidomimetic assembly derived from a carbohydrate
Author(s) -
Chung YingKit,
Claridge Timothy D. W.,
Fleet George W. J.,
Johnson Stephen W.,
Jones John H.,
Lumbard Keith W.,
Stachulski Andrew V.
Publication year - 2004
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.488
Subject(s) - peptidomimetic , trimer , chemistry , dimer , tetramer , monomer , saponification , carbohydrate , dipeptide , stereochemistry , component (thermodynamics) , amino acid , combinatorial chemistry , organic chemistry , peptide , biochemistry , polymer , enzyme , physics , thermodynamics
A strategy has been established for the synthesis of peptidomimetics derived from unsaturated carbohydrates, and exemplified by the use of methyl 2,6‐anhydro‐7‐azido‐3,7‐deoxy‐4,5‐ O ‐isopropylidene‐ D ‐ lyxo ‐hept‐2‐enonate 9 as a dipeptide ‘monomer’ which can be elaborated from either end. Selective reduction of 9 gives a protected pseudodipeptide ester suitable for use as an amino component, and saponification gives an azido acid suitable for use as a carboxyl component. The ‘dimer’ product of coupling these two components with TBTU can be similarly elaborated at either end to give a ‘trimer’, and a further cycle of selective reduction and coupling gave a ‘tetramer’, 17 , a pseudo‐octapeptide. Copyright © 2003 European Peptide Society and John Wiley & Sons, Ltd.