The Synthesis of Some Oligopeptides Derived from Novel Carbohydrate α-Amino Acids

Adrian Scaffidi, Brian Skelton, Robert Stick, Allan White

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The attempted coupling of a carbohydrate alpha-azido acid with a carbohydrate alpha-amino ester in the presence of a diimide, hopefully to produce a dipeptide, yielded only the carboxylic anhydride. However, the combination of 4-toluenesulfonyl chloride in pyridine was successful, and four carbohydrate dipeptides were separately produced. One of these dipeptides was further transformed into a tripeptide, and another into a hexapeptide. A single-crystal X-ray structure is reported for (3S)-3-azido-3-C-carboxy-3-deoxy-1,2: 5,6-di-O-isopropylidene-alpha-D-ribo-hexose, amide with (3S)-3-amino-3-deoxy-1,2: 5,6-di-O-isopropylidene-3-C-methoxycarbonyl-alpha-D-ribo-hexose.
Original languageEnglish
Pages (from-to)733-740
JournalAustralian Journal of Chemistry
Volume57
Issue number8
DOIs
Publication statusPublished - 2004

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