The Solution Conformational Preferences of the Sugar and Sugar Phosphate Constituents of RNA and DNA

John Alan Gerlt, A. Virginia Youngblood

Research output: Contribution to journalArticle

Abstract

The analysis of the proton NMR spectra of stereospecifically deuterated (S)-tetrahydrofuranmethanol, methyl β-D-ribofuranoside, methyl β-D-2-deoxyribofuranoside, and the 5-phosphates of the sugar acetals leads to several important and previously unrecognized observations about the determinants of the solution conformations of nucleosides and nucleotides: (1) in the unsubstituted sugars and their phosphates, the preferred furanoside ring conformation is the 3'-endo pucker and not the 2'-endo pucker observed in most nucleosides and nucleotides; (2) in the unsubstituted sugars and their phosphates, the gauche-gauche rotamer about the C4-C5 bond does not predominate as is found in the nucleosides and nucleotides but rather the two rotamers in which the vicinal C-0 bonds are gauche to one another (gauche-gauche and gauche-trans) are about equally favored; (3) the observed predominant occurrence of the gauche-gauche rotamer about the C4-C5' bond in nucleosides and nucleotides is presumably the result of an interaction between the substituent on C5' and the heterocyclic base, which is made more favorable by a shift in the furanoside ring conformation; and (4) the rotameric distribution about the C5-O5 bonds in the sugar acetal phosphates is the same as that observed in nucleosides and nucleotides. These observations suggest that the nature of the furanoside ring conformation and the rotameric distributions about the C4-C5' and C5O5' bonds may not be as intimately interdependent as previously believed.

Original languageEnglish (US)
Pages (from-to)7433-7438
Number of pages6
JournalJournal of the American Chemical Society
Volume102
Issue number25
DOIs
StatePublished - Dec 1980
Externally publishedYes

Fingerprint

Sugar Phosphates
Nucleotides
RNA
Nucleosides
Sugars
sugar
DNA
phosphate
Conformations
Phosphates
Acetals
nuclear magnetic resonance
Protons
Nuclear magnetic resonance
distribution

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

The Solution Conformational Preferences of the Sugar and Sugar Phosphate Constituents of RNA and DNA. / Gerlt, John Alan; Virginia Youngblood, A.

In: Journal of the American Chemical Society, Vol. 102, No. 25, 12.1980, p. 7433-7438.

Research output: Contribution to journalArticle

@article{c1ecabd73e4b4fe5b9c4355801fe70d0,
title = "The Solution Conformational Preferences of the Sugar and Sugar Phosphate Constituents of RNA and DNA",
abstract = "The analysis of the proton NMR spectra of stereospecifically deuterated (S)-tetrahydrofuranmethanol, methyl β-D-ribofuranoside, methyl β-D-2-deoxyribofuranoside, and the 5-phosphates of the sugar acetals leads to several important and previously unrecognized observations about the determinants of the solution conformations of nucleosides and nucleotides: (1) in the unsubstituted sugars and their phosphates, the preferred furanoside ring conformation is the 3'-endo pucker and not the 2'-endo pucker observed in most nucleosides and nucleotides; (2) in the unsubstituted sugars and their phosphates, the gauche-gauche rotamer about the C4-C5 bond does not predominate as is found in the nucleosides and nucleotides but rather the two rotamers in which the vicinal C-0 bonds are gauche to one another (gauche-gauche and gauche-trans) are about equally favored; (3) the observed predominant occurrence of the gauche-gauche rotamer about the C4-C5' bond in nucleosides and nucleotides is presumably the result of an interaction between the substituent on C5' and the heterocyclic base, which is made more favorable by a shift in the furanoside ring conformation; and (4) the rotameric distribution about the C5-O5 bonds in the sugar acetal phosphates is the same as that observed in nucleosides and nucleotides. These observations suggest that the nature of the furanoside ring conformation and the rotameric distributions about the C4-C5' and C5O5' bonds may not be as intimately interdependent as previously believed.",
author = "Gerlt, {John Alan} and {Virginia Youngblood}, A.",
year = "1980",
month = "12",
doi = "10.1021/ja00545a005",
language = "English (US)",
volume = "102",
pages = "7433--7438",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "25",

}

TY - JOUR

T1 - The Solution Conformational Preferences of the Sugar and Sugar Phosphate Constituents of RNA and DNA

AU - Gerlt, John Alan

AU - Virginia Youngblood, A.

PY - 1980/12

Y1 - 1980/12

N2 - The analysis of the proton NMR spectra of stereospecifically deuterated (S)-tetrahydrofuranmethanol, methyl β-D-ribofuranoside, methyl β-D-2-deoxyribofuranoside, and the 5-phosphates of the sugar acetals leads to several important and previously unrecognized observations about the determinants of the solution conformations of nucleosides and nucleotides: (1) in the unsubstituted sugars and their phosphates, the preferred furanoside ring conformation is the 3'-endo pucker and not the 2'-endo pucker observed in most nucleosides and nucleotides; (2) in the unsubstituted sugars and their phosphates, the gauche-gauche rotamer about the C4-C5 bond does not predominate as is found in the nucleosides and nucleotides but rather the two rotamers in which the vicinal C-0 bonds are gauche to one another (gauche-gauche and gauche-trans) are about equally favored; (3) the observed predominant occurrence of the gauche-gauche rotamer about the C4-C5' bond in nucleosides and nucleotides is presumably the result of an interaction between the substituent on C5' and the heterocyclic base, which is made more favorable by a shift in the furanoside ring conformation; and (4) the rotameric distribution about the C5-O5 bonds in the sugar acetal phosphates is the same as that observed in nucleosides and nucleotides. These observations suggest that the nature of the furanoside ring conformation and the rotameric distributions about the C4-C5' and C5O5' bonds may not be as intimately interdependent as previously believed.

AB - The analysis of the proton NMR spectra of stereospecifically deuterated (S)-tetrahydrofuranmethanol, methyl β-D-ribofuranoside, methyl β-D-2-deoxyribofuranoside, and the 5-phosphates of the sugar acetals leads to several important and previously unrecognized observations about the determinants of the solution conformations of nucleosides and nucleotides: (1) in the unsubstituted sugars and their phosphates, the preferred furanoside ring conformation is the 3'-endo pucker and not the 2'-endo pucker observed in most nucleosides and nucleotides; (2) in the unsubstituted sugars and their phosphates, the gauche-gauche rotamer about the C4-C5 bond does not predominate as is found in the nucleosides and nucleotides but rather the two rotamers in which the vicinal C-0 bonds are gauche to one another (gauche-gauche and gauche-trans) are about equally favored; (3) the observed predominant occurrence of the gauche-gauche rotamer about the C4-C5' bond in nucleosides and nucleotides is presumably the result of an interaction between the substituent on C5' and the heterocyclic base, which is made more favorable by a shift in the furanoside ring conformation; and (4) the rotameric distribution about the C5-O5 bonds in the sugar acetal phosphates is the same as that observed in nucleosides and nucleotides. These observations suggest that the nature of the furanoside ring conformation and the rotameric distributions about the C4-C5' and C5O5' bonds may not be as intimately interdependent as previously believed.

UR - http://www.scopus.com/inward/record.url?scp=0001183729&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001183729&partnerID=8YFLogxK

U2 - 10.1021/ja00545a005

DO - 10.1021/ja00545a005

M3 - Article

AN - SCOPUS:0001183729

VL - 102

SP - 7433

EP - 7438

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 25

ER -