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Title: Elucidation of the conformational properties of N-formylglycine dithio acid by ab initio SCF-MO calculations
Authors: Fausto, R. 
Teixeira-Dias, J. J. C. 
Carey, P. R. 
Issue Date: Mar-1991
Publisher: American Chemical Society
Citation: Journal of the American Chemical Society. 113:7 (1991) 2471-2476
Abstract: Ab initio SCF-MO calculations were carried out for the molecule N-formylglycine dithio acid using STO-3G and 3-21G basis sets. Structures and energies of several conformations of this molecule determined by gradient geometry refinement are reported, and some conformationally dependent local geometry trends discussed. For conformations involving rotational isomerism about the NH-CH2 and CH,-C(=S) single bonds, the 3-21G results reveal the presence of three conformational states. These conformers are strikingly similar to those determined for glycine dithio esters by X-ray crystallographic and vibrational spectroscopic analyses. One conformer has a small NH-CH2-C-S(thi,,l, torsional angle and close N-to-S(thiol) atom contact. The calculations provide a description of this N.4 nonbonded interaction which has implications for the structure and reactivity of enzyme-substrate complexes which incorporate a similar contact. However, no evidence is found for favorable N-to-S(,hi,,,,) interactions for the conformer which has a small NH-CH2-C=S torsional angle.
ISSN: 0002-7863
DOI: 10.1021/ja00007a019
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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