ISSN:
0899-0042
Keywords:
cyclopropylpyrroloindole
;
adozelesin
;
carzelesin
;
left-handed conformation
;
circular dichroism
;
Chemistry
;
Food Science, Agricultural, Medicinal and Pharmaceutical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The purpose of this work was to determine the conformation adopted in solution by adozelesin, carzelesin, and their derivatives obtained under basic or acidic conditions. Circular dichroism in the 270-330 nm wavelengths region was studied. In solution adozelesin can adopt two different conformations: a left-handed one which is thermodynamically favoured at low temperature and is mainly present at room temperature, and a right-handed one which is observed either at high temperature or at room temperature in the presence of DNA. This was ascertained by the presence of circular dichroism signals of the couplet type. The active form of carzelesin, i.e., U-76074, also exhibited a left-handed conformation in solution. Carzelesin and the derivatives obtained under acidic conditions that lack the cyclopropyl ring, and cyclopropylpyrroloindole, obtained under basic conditions, cannot adopt such a conformation. Chirality 8:585-589, 1996. © 1997 Wiley-Liss, Inc.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
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