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The synthesis of oligomers of oxetane-based dipeptide isosteres derived from L-rhamnose or D-xylose.

Abstract:

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 ...

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Publication status:
Published

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Publisher copy:
10.1002/psc.622

Authors


Johnson, SW More by this author
Jenkinson, SF More by this author
Pérez-Victoria, I More by this author
Claridge, TD More by this author
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Journal:
Journal of peptide science : an official publication of the European Peptide Society
Volume:
11
Issue:
6
Pages:
303-318
Publication date:
2005-06-05
DOI:
EISSN:
1099-1387
ISSN:
1075-2617
URN:
uuid:c8428cb7-d3a4-4579-a827-e90e379d4bba
Source identifiers:
39556
Local pid:
pubs:39556

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