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Multinuclear magnetic resonance, electrospray ionization–mass spectroscopy, and parametric method 5 studies of a new derivative of gossypol with 2‐thiophenecarbohydrazide as well as its complexes with LI + , Na + , K + , RB + , and Cs + cations
Author(s) -
Przybylski Piotr,
Schilf Wojciech,
Lewandowska Weronika,
Brzezinski Bogumil
Publication year - 2006
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.20548
Subject(s) - chemistry , electrospray ionization , tautomer , derivative (finance) , stoichiometry , nuclear magnetic resonance spectroscopy , hydrogen bond , mass spectrometry , spectroscopy , crystallography , gossypol , intramolecular force , computational chemistry , stereochemistry , molecule , organic chemistry , biochemistry , physics , chromatography , quantum mechanics , financial economics , economics
A new derivative of racemic gossypol with 2‐thiophenecarbohydrazide (GHHT) and its complexes with monovalent cations have been synthesized and studied by electrospray ionization–mass spectroscopy (ESI‐MS), multinuclear nuclear magnetic resonance (NMR), as well as by the Parametric Method 5 (PM5) methods. It is demonstrated that GHHT forms stable complexes of 1:1 stoichiometry with monovalent metal cations. The structures of the complexes are stabilized by three types of intramolecular hydrogen bonds. The spectroscopic methods have provided clear evidence that GHHT and its complexes exist in the DMSO‐d 6 solution in the N‐imine–N‐imine tautomeric forms. The structures of the GHHT and its complexes with Li + , Na + , K + , Rb + , and Cs + cations are visualized and discussed in detail. © 2006 Wiley Periodicals, Inc. Biopolymers 83: 213–225, 2006 This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com