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Synthesis and structural studies of oligomers of 6-amino-2,5-anhydro-6-deoxy-d-mannonic acid

✍ Scribed by T.K Chakraborty; S Jayaprakash; P Srinivasu; M Govardhana Chary; P.V Diwan; R Nagaraj; A Ravi Sankar; A.C Kunwar

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 78 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01425-8

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✦ Synopsis

A novel cycloetherification process involving a facile 5-exo S N 2-type ring closure by intramolecular opening of a terminal aziridine ring by a g-hydroxyl group, led to the stereoselective synthesis of 6-amino-2,5-anhydro-6-deoxy-D-mannonic acid (1). Oligomerization of 1 by solution phase peptide coupling methods gave oligomers 2-5. While most of the oligomers, in either protected or deprotected form, did not show any significant secondary structure, octamer 5 (P=H) exhibited a very strong positive band at 216 nm in its CD spectrum in MeOH and TFE, indicating the possibility of the presence of an ordered structure in solution. Its 1 H NMR spectra in various polar solvents, however, failed to produce any distinct dispersion of the amide proton chemical shifts. Compounds 1-5 were found to be inactive in hypoglyceamic tests in rats.

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