The Synthesis of Some Oligopeptides Derived from Novel Carbohydrate α-Amino Acids
Adrian Scaffidi A , Brian W. Skelton A , Robert V. Stick A B and Allan H. White AA Chemistry, School of Biomedical and Chemical Sciences M313, University of Western Australia, Crawley WA 6009, Australia.
B Author to whom correspondence should be addressed (e-mail: rvs@chem.uwa.edu.au).
Australian Journal of Chemistry 57(8) 733-740 https://doi.org/10.1071/CH04014
Submitted: 22 January 2004 Accepted: 5 March 2004 Published: 10 August 2004
Abstract
The attempted coupling of a carbohydrate α-azido acid with a carbohydrate α-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-α-d-ribo-hexose, amide with (3S)-3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methoxycarbonyl-α-d-ribo-hexose.
Acknowledgment
We thank Simon Brayshaw for suggesting the tosyl chloride/pyridine procedure to us.
[1]
A. Scaffidi,
B. W. Skelton,
R. V. Stick,
A. H. White,
Aust. J. Chem. 2004, 57, 735.
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
| Crossref | GoogleScholarGoogle Scholar |
[9]
