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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/3765

Title: CONFORMATIONAL-ANALYSIS OF RING-A AND TOTAL ASSIGNMENT OF 19-FUNCTIONALIZED 4-EN-3-ONE STEROIDS - APPLICABILITY OF 2D NOE AS A CRUCIAL TECHNIQUE
Authors: DESAI, UR
TRIVEDI, GK
Keywords: nuclear magnetic-resonance
dimensional nmr-spectroscopy
coupling-constants
2-dimensional spectroscopy
chemical-shifts
h-1-nmr
proteins
equation
protons
c-13
Issue Date: 1991
Publisher: AMER CHEMICAL SOC
Citation: JOURNAL OF ORGANIC CHEMISTRY, 56(15), 4625-4631
Abstract: The conformational analysis of ring A of 4-en-3-one steroids with three kinds of functionalizations viz. the 19-hydroxy, 19-oxo, and the 6-beta,19-epoxy groups, is discussed using a simple protocol-COSY 90 + NOESY + HETCOR. The 2D NOE technique is found to be of immense importance in deducing the conformational preferences of these steroids. The conformations are derived by connectivity pattern analysis and independently by torsional angle calculations employing the Karplus equation. While steroids 1 and 2 show ''normal'' 1-alpha,2-beta half-chair conformation, steroid 3 exhibits ring A in the 1-beta,2-alpha ''inverted'' conformation. The conformational analysis highlights aspects like interactions of the 1,3-diaxial type and the effect of tilting the 19-carbon toward ring A or ring B. A comment is made to that effect.
URI: http://dx.doi.org/10.1021/jo00015a012
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3765
http://hdl.handle.net/10054/3765
ISSN: 0022-3263
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