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Stereochemical studies on esperamicins: Determination of the absolute configuration of hydroxyamino sugar fragment.

โœ Scribed by J. Golik; H. Wong; B. Krishnan; D.M. Vyas; T.W. Doyle


Book ID
104219956
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
219 KB
Volume
32
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The 0-D-gluco-hexopyranose configuration has been assigned for the hydroxyamino sugar fragment of esperamicin A'. This determination concluded our study on the absolute configuration of the carbohydrate portion of esperamicins. Since our first report on the structure elucidation of esperamicins A,, AZ and Alb in 1987' we have focused our efforts on determination of their absolute configuration. In the course of these studies, involving chemical degradations, spectroscopy and x-ray methods, we have established the L


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The absolute stereochmistry of the isopropylamino sugar moiety of esperamicin A1 was determined as the g-&-threo-pentopyranosyl by comparing the CD spectra of derivatized methanolysis product 4 with those of two synthesized antipodal glycosides 2 and Is.

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