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The role of configuration and conformation in the binding of 2,3‐benzodiazepines to human serum albumin
Author(s) -
Visy Julia,
Simonyi Miklós
Publication year - 1989
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530010405
Subject(s) - chemistry , substituent , human serum albumin , steric effects , stereochemistry , dihedral angle , diazepine , serum albumin , molecule , bovine serum albumin , ring (chemistry) , organic chemistry , chromatography , biochemistry , hydrogen bond
2,3‐Benzodiazepines containing a centre of asymmetry at C‐5 possess both central and helical chiralities, and the solution of their racemates contains four molecular species. The binding of these compounds to human serum albumin (HSA) was studied by affinity chromatography. The binding strength depended both on the steric orientation of the 5‐ethyl substituent and on the conformation of the diazepine ring. Conformation P (defined by the positive sign of C‐1–N‐2‐N–3–C‐4 torsion angle) is favoured, while the quasiaxial orientation ‐of the 5‐ethyl substituent is not favoured by the albumin molecule.