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The synthesis of oligomers of oxetane‐based dipeptide isosteres derived from L ‐rhamnose or D ‐xylose
Author(s) -
Johnson Stephen W.,
Jenkinson née Barker Sarah F.,
Angus Donald,
PérezVictoria Ignacio,
Claridge Timothy D. W.,
Fleet George W. J.,
Jones John H.
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.622
Subject(s) - dipeptide , oxetane , xylose , rhamnose , chemistry , stereochemistry , organic chemistry , biochemistry , amino acid , polysaccharide , fermentation
Routes to oligomers (dimers, tetramers, hexamers) of five oxetane‐based dipeptide isosteres have been established. Methyl 2,4‐anhydro‐5‐azido‐5‐deoxy‐ L ‐rhamnonate ‘monomer’ led, by coupling the corresponding carboxylic acid and amine, to a ‘dimer’. Reverse‐aldol ring‐opening occurred on attempted saponification of the dimer, so all further oligomerization was performed using TBDMS C‐3 hydroxyl protection. The silyl protected L ‐rhamnonate monomer led in turn to the dimer (via the monomer acid and amine), the tetramer (via the dimer acid and amine) and finally the hexamer (via the tetramer acid and dimer amine). In each case the acids were obtained through saponification of the respective methyl esters and the amines were obtained by hydrogenation of the azides; coupling was TBTU‐mediated. Essentially the same strategy was employed on equivalent D ‐lyxonate, 6‐deoxy‐ L ‐altronate, 6‐deoxy‐ D ‐gulonate and D ‐fuconate dipeptide isosteres to give the respective dimers, tetramers and hexamers. Copyright © 2004 European Peptide Society and John Wiley & Sons, Ltd.