Premium
PCILO study of the conformation of 20‐oxopregnane hormones
Author(s) -
Viana Luci Martins,
Takahata Yuji
Publication year - 1982
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560220205
Subject(s) - chemistry , intramolecular force , hormone , hydrogen bond , side chain , absolute deviation , computational chemistry , stereochemistry , molecule , organic chemistry , biochemistry , statistics , mathematics , polymer
PCILO calculations on conformations of the C‐17 side chains of three 20‐oxopregnane hormones, progesterone, corticosterone, and cortisol, reveal that the calculated conformations are generally in close agreement with those observed crystallographically. Average deviation of the calculated rotation angle around the C(17)—C(20) bond from the experiment is 9°. The PCILO calculations also predict the intramolecular hydrogen bond between the 20‐carbonyl group and the 21‐hydroxyl for the three hormones. This is in accordance with experiment. It was concluded that the PCILO method is reliable in predicting conformations of the side chains of hormones whereas the extended Hückel theory ( EHT ) predicted wrong conformations. Based upon the PCILO calculations, biological activities of the hormones are discussed.