Binding properties of carbohydrate sulfamates based on ab initio 6-31 + G** calculations on N-methyl and N-ethyl sulfamate anions

Dennis M. Whitfield, Doriano Lamba, Ting Hua Tang, I. Csizmadia

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

2-Deoxy-2-sulfoamino-D-glucopyranoside anions are uniquely found in heparin-like biopolymers. Due to the bioactivities of these biopolymers, there is considerable interest in developing heparin mimetics as potential therapeutic agents. The chemical bonding of such anions is analyzed by topological analysis of the electron-density distribution based on ab initio 6-31 + G** calculations. The results support an amine-like pyramidal geometry for nitrogen with a well-defined maximum in the Laplacian of the charge density consistent with a lone pair of electrons. Water complexes of the N-methyl sulfamate anions give insight into binding motifs, including bifurcated hydrogen-bonded systems and hydrogen-bond properties for the sulfoamino nitrogen. Finally, by systematic variation of the structural parameters of these N-alkyl sulfamate anions, MM + parameters for this group in sugars were determined. The structural properties calculated by molecular modeling agree well with the ab initio results and with three crystal structures of sodium 2-deoxy-2-sulfoamino-α-D-glucopyranose derivatives.

Original languageEnglish
Pages (from-to)17-39
Number of pages23
JournalCarbohydrate Research
Volume286
DOIs
Publication statusPublished - Jun 5 1996

Fingerprint

Anions
Carbohydrates
Biopolymers
Heparin
Hydrogen
Nitrogen
Electrons
Electronic density of states
Molecular modeling
Bioactivity
Charge density
Sugars
Amines
Structural properties
Hydrogen bonds
Crystal structure
Sodium
Derivatives
Geometry
sulfamic acid

Keywords

  • 2-deoxy-2-sulfoamino-
  • ab initio calculations
  • D-glucopyranoside
  • heparin
  • sulfamate, N-ethyl-
  • sulfamate, N-methyl-

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Binding properties of carbohydrate sulfamates based on ab initio 6-31 + G** calculations on N-methyl and N-ethyl sulfamate anions. / Whitfield, Dennis M.; Lamba, Doriano; Tang, Ting Hua; Csizmadia, I.

In: Carbohydrate Research, Vol. 286, 05.06.1996, p. 17-39.

Research output: Contribution to journalArticle

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N2 - 2-Deoxy-2-sulfoamino-D-glucopyranoside anions are uniquely found in heparin-like biopolymers. Due to the bioactivities of these biopolymers, there is considerable interest in developing heparin mimetics as potential therapeutic agents. The chemical bonding of such anions is analyzed by topological analysis of the electron-density distribution based on ab initio 6-31 + G** calculations. The results support an amine-like pyramidal geometry for nitrogen with a well-defined maximum in the Laplacian of the charge density consistent with a lone pair of electrons. Water complexes of the N-methyl sulfamate anions give insight into binding motifs, including bifurcated hydrogen-bonded systems and hydrogen-bond properties for the sulfoamino nitrogen. Finally, by systematic variation of the structural parameters of these N-alkyl sulfamate anions, MM + parameters for this group in sugars were determined. The structural properties calculated by molecular modeling agree well with the ab initio results and with three crystal structures of sodium 2-deoxy-2-sulfoamino-α-D-glucopyranose derivatives.

AB - 2-Deoxy-2-sulfoamino-D-glucopyranoside anions are uniquely found in heparin-like biopolymers. Due to the bioactivities of these biopolymers, there is considerable interest in developing heparin mimetics as potential therapeutic agents. The chemical bonding of such anions is analyzed by topological analysis of the electron-density distribution based on ab initio 6-31 + G** calculations. The results support an amine-like pyramidal geometry for nitrogen with a well-defined maximum in the Laplacian of the charge density consistent with a lone pair of electrons. Water complexes of the N-methyl sulfamate anions give insight into binding motifs, including bifurcated hydrogen-bonded systems and hydrogen-bond properties for the sulfoamino nitrogen. Finally, by systematic variation of the structural parameters of these N-alkyl sulfamate anions, MM + parameters for this group in sugars were determined. The structural properties calculated by molecular modeling agree well with the ab initio results and with three crystal structures of sodium 2-deoxy-2-sulfoamino-α-D-glucopyranose derivatives.

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