An exploratory ab initio conformational analysis of selected fragments of nicotinamide adenine dinucleotide (NAD+). Part I: 5-Deoxyribose nicotinamide N-glycoside

Suzanne K. Lau; Gregory A. Chass; Sándor Lovas; Botond Penke; Imre G. Csizmadia

doi:10.1016/j.theochem.2003.08.117

An exploratory ab initio conformational analysis of selected fragments of nicotinamide adenine dinucleotide (NAD⁺). Part I: 5-Deoxyribose nicotinamide N-glycoside

Suzanne K. Lau, Gregory A. Chass, Sándor Lovas, Botond Penke, Imre G. Csizmadia

Department of Biomedical Sciences

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

Ab initio molecular orbital computations were carried out on selected fragments of Nicotinamide Adenine Dinucleotide (NAD⁺) at the RHF/3-21G and RHF/6-31G(d) levels of theory. The focus of this work was on the nicotinamide-ribose moiety. In this model study, the ribose was replaced by 5-deoxyribose. Key points of examination included the rotation of the carboxyamide functionality, rotors between the nicotinamide and ribose rings as well as ring puckering in the ribose sugar. The structural definitions of the adenosine fragment and diphosphate chain were defined herein, facilitating future theoretical investigation. A preliminary attempt was made to refine the results at the elevated RHF/6-31G and RHF/6-31g(d) basis sets. The former showed results in agreement with the RHF/3-21G data sets, whereas the inclusion of preliminary polarization showed deviance in the χ_i ¹ dihedral of the a[g^-a] conformer.

Original language	English (US)
Pages (from-to)	415-429
Number of pages	15
Journal	Journal of Molecular Structure: THEOCHEM
Volume	666-667
DOIs	https://doi.org/10.1016/j.theochem.2003.08.117
State	Published - Dec 29 2003

All Science Journal Classification (ASJC) codes

Biochemistry
Condensed Matter Physics
Physical and Theoretical Chemistry

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10.1016/j.theochem.2003.08.117

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An exploratory ab initio conformational analysis of selected fragments of nicotinamide adenine dinucleotide (NAD⁺). Part I: 5-Deoxyribose nicotinamide N-glycoside. / Lau, Suzanne K.; Chass, Gregory A.; Lovas, Sándor et al.
In: Journal of Molecular Structure: THEOCHEM, Vol. 666-667, 29.12.2003, p. 415-429.

Research output: Contribution to journal › Article › peer-review

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title = "An exploratory ab initio conformational analysis of selected fragments of nicotinamide adenine dinucleotide (NAD+). Part I: 5-Deoxyribose nicotinamide N-glycoside",

abstract = "Ab initio molecular orbital computations were carried out on selected fragments of Nicotinamide Adenine Dinucleotide (NAD+) at the RHF/3-21G and RHF/6-31G(d) levels of theory. The focus of this work was on the nicotinamide-ribose moiety. In this model study, the ribose was replaced by 5-deoxyribose. Key points of examination included the rotation of the carboxyamide functionality, rotors between the nicotinamide and ribose rings as well as ring puckering in the ribose sugar. The structural definitions of the adenosine fragment and diphosphate chain were defined herein, facilitating future theoretical investigation. A preliminary attempt was made to refine the results at the elevated RHF/6-31G and RHF/6-31g(d) basis sets. The former showed results in agreement with the RHF/3-21G data sets, whereas the inclusion of preliminary polarization showed deviance in the χi 1 dihedral of the a[g-a] conformer.",

author = "Lau, {Suzanne K.} and Chass, {Gregory A.} and S{\'a}ndor Lovas and Botond Penke and Csizmadia, {Imre G.}",

note = "Funding Information: This work was supported with grants from the Global Institute Of COmputational Molecular and Materials Sciences (GIOCOMMS), Toronto, Ontario, Canada. S. Lovas would like to acknowledge the support from the BRIN Program of the National Center for Research (NIH Grant Number 1 P20 RR16469) and from the National Science Foundation (EPS-0091900). Thanks are extended to Jacqueline M.S. Law, Christopher N.J. Marai, Jeremy H. Keller, Michelle A. Sahai and David H. Setiadi for helpful discussion. ",

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AU - Csizmadia, Imre G.

N1 - Funding Information: This work was supported with grants from the Global Institute Of COmputational Molecular and Materials Sciences (GIOCOMMS), Toronto, Ontario, Canada. S. Lovas would like to acknowledge the support from the BRIN Program of the National Center for Research (NIH Grant Number 1 P20 RR16469) and from the National Science Foundation (EPS-0091900). Thanks are extended to Jacqueline M.S. Law, Christopher N.J. Marai, Jeremy H. Keller, Michelle A. Sahai and David H. Setiadi for helpful discussion.

PY - 2003/12/29

Y1 - 2003/12/29

N2 - Ab initio molecular orbital computations were carried out on selected fragments of Nicotinamide Adenine Dinucleotide (NAD+) at the RHF/3-21G and RHF/6-31G(d) levels of theory. The focus of this work was on the nicotinamide-ribose moiety. In this model study, the ribose was replaced by 5-deoxyribose. Key points of examination included the rotation of the carboxyamide functionality, rotors between the nicotinamide and ribose rings as well as ring puckering in the ribose sugar. The structural definitions of the adenosine fragment and diphosphate chain were defined herein, facilitating future theoretical investigation. A preliminary attempt was made to refine the results at the elevated RHF/6-31G and RHF/6-31g(d) basis sets. The former showed results in agreement with the RHF/3-21G data sets, whereas the inclusion of preliminary polarization showed deviance in the χi 1 dihedral of the a[g-a] conformer.

AB - Ab initio molecular orbital computations were carried out on selected fragments of Nicotinamide Adenine Dinucleotide (NAD+) at the RHF/3-21G and RHF/6-31G(d) levels of theory. The focus of this work was on the nicotinamide-ribose moiety. In this model study, the ribose was replaced by 5-deoxyribose. Key points of examination included the rotation of the carboxyamide functionality, rotors between the nicotinamide and ribose rings as well as ring puckering in the ribose sugar. The structural definitions of the adenosine fragment and diphosphate chain were defined herein, facilitating future theoretical investigation. A preliminary attempt was made to refine the results at the elevated RHF/6-31G and RHF/6-31g(d) basis sets. The former showed results in agreement with the RHF/3-21G data sets, whereas the inclusion of preliminary polarization showed deviance in the χi 1 dihedral of the a[g-a] conformer.

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An exploratory ab initio conformational analysis of selected fragments of nicotinamide adenine dinucleotide (NAD⁺). Part I: 5-Deoxyribose nicotinamide N-glycoside

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