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Quantum chemical studies on the conformational structure of bacterial peptidoglycan. V. PCILO Calculations on β(1 → 4) linked disaccharide of N‐acetyl‐glucosamine and N‐acetyl muramic acid
Author(s) -
Yadav Janardan Singh
Publication year - 1983
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.560230426
Subject(s) - muramic acid , peptidoglycan , chemistry , disaccharide , glycan , amino sugar , n acetylglucosamine , glucosamine , stereochemistry , moiety , aminosugar , molecule , crystallography , biochemistry , cell wall , organic chemistry , glycoprotein , enzyme
The glycan moiety of the bacterial peptidoglycan consists of alternatingly β(1 → 4) linked disaccharides of N‐acetylglucosamine (NAG) and its 3‐O‐D lactic derivative, N‐acetyl β‐D‐muramic acid (NAM). PCILO conformational energy calculations have been carried out for NAG–NAM and NAM–NAG disaccharides to see whether or not the glycan strands possess a chitinlike structure as suggested by earlier workers. In agrement with recent experimental findings, the present results also suggest that the chitinlike structure is energetically disallowed. Furthermore, the bulky N‐acetyl substituents at C 2 positions of the two sugar molecules are found to be relatively less important in stabilizing mutual orientations of the two pyranosyl rings.