The solution conformation of the homogeneous, heparin-derived tetrasaccharide ΔUA2S(1 → 4)-α-d-GlcNpS6S(1 → 4)-α-l-IdoAp2S(1 → 4)-α-d-GlcNpS6S (residues A, B, C and D respectively, where IdoA is iduronic acid) has been investigated by using 1H- and 13C-NMR. Ring conformations have been defined by J-coupling constants and inter-proton nuclear Overhauser effects (NOEs), and the orientation of one ring with respect to the other has been defined by inter-ring NOEs. NOE-based conformational modelling has been done by using the iterative relaxation matrix approach (IRMA), restrained molecular dynamics simulations and energy minimization to refine structures and to distinguish between minor structural differences and equilibria between various ring forms. Both glucosamine residues B and D are in the 4C1 chair conformation. The 6-O-sulphate group is oriented in the gauche–trans configuration in the D ring, whereas in the B ring the gauche–gauche rotomer predominates. Uronate (A) and iduronate (C) residues are mostly represented by 1H2 and 2S0 twisted boat forms, respectively, with small deviations in expected coupling constants and NOEs suggesting minor contributions from other A and C ring conformations.
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August 1996
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Research Article|
August 15 1996
NMR solution conformation of heparin-derived tetrasaccharide
Dmitri MIKHAILOV;
Dmitri MIKHAILOV
*Departments of Biochemistry and Laboratory of Medicine and Pathology, Biomedical Engineering Center, University of Minnesota Medical School, 420 Delaware Street, S.E., Minneapolis, MN 55455, U.S.A.
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Kevin H. MAYO;
Kevin H. MAYO
‡
*Departments of Biochemistry and Laboratory of Medicine and Pathology, Biomedical Engineering Center, University of Minnesota Medical School, 420 Delaware Street, S.E., Minneapolis, MN 55455, U.S.A.
‡To whom correspondence should be addressed.
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Ioncho R. VLAHOV;
Ioncho R. VLAHOV
†Department of Medicinal and Natural Products Chemistry, College of Pharmacy, The University of Iowa, 115 S. Grand Ave., Iowa City, IA 52242, U.S.A
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Toshihiko TOIDA;
Toshihiko TOIDA
†Department of Medicinal and Natural Products Chemistry, College of Pharmacy, The University of Iowa, 115 S. Grand Ave., Iowa City, IA 52242, U.S.A
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Azra PERVIN;
Azra PERVIN
†Department of Medicinal and Natural Products Chemistry, College of Pharmacy, The University of Iowa, 115 S. Grand Ave., Iowa City, IA 52242, U.S.A
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Robert J. LINHARDT
Robert J. LINHARDT
†Department of Medicinal and Natural Products Chemistry, College of Pharmacy, The University of Iowa, 115 S. Grand Ave., Iowa City, IA 52242, U.S.A
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Publisher: Portland Press Ltd
Received:
February 29 1996
Revision Received:
April 18 1996
Accepted:
April 23 1996
Online ISSN: 1470-8728
Print ISSN: 0264-6021
The Biochemical Society, London © 1996
1996
Biochem J (1996) 318 (1): 93–102.
Article history
Received:
February 29 1996
Revision Received:
April 18 1996
Accepted:
April 23 1996
Citation
Dmitri MIKHAILOV, Kevin H. MAYO, Ioncho R. VLAHOV, Toshihiko TOIDA, Azra PERVIN, Robert J. LINHARDT; NMR solution conformation of heparin-derived tetrasaccharide. Biochem J 15 August 1996; 318 (1): 93–102. doi: https://doi.org/10.1042/bj3180093
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