Oxidation of threose-series pentoses and hexoses by sodium N-chloro-p- toluenesulfonamide

Kanchugarakoppal S. Rangappa, Huchappa Manjunathaswamy, Manikanahally P. Raghavendra, Channe Gowda

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

The kinetics and mechanism of oxidation of threose-series hexoses and pentoses by chloramine-T in alkaline medium was investigated. Kinetic studies with D-galactose, D-sorbose, D-xylose, and D-lyxose showed that the rate of the reaction was first order with respect to sugar and chloramine-T, and second order with respect to hydroxide ion. p-Toluenesulfonamide and chloride ions, the reduced products of chloramine-T, have no effect on the reaction rate. The rate increases with increase in ionic strength of the medium, and the dielectric effect is negative. Proton inventory studies in H2O-D2O mixtures suggested a single transition state. Product analysis for D-gulose, Didose, L-sorbose, D-galactose, D-talose, D-tagatose, D-xylose, and D-lyxose revealed that all lyxoseseries hexoses gave mainly mixtures of lyxonic and threonic acids with minor proportions of hexonic, xylonic and glyceric acids, whereas all xylose-series hexoses gave mixtures of lyxonic, threonic and glyceric acids with minor amounts of xylonic and hexonic acids. Xylose and lyxose gave mixtures consisting mainly of lyxonic, threonic, and glyceric acids with minor proportions of xylonic acid. From the results of kinetic studies, reaction stoichiometry, and product analysis, a possible mechanism for the oxidation of threose-series sugars with chloramine-T is suggested.

Original languageEnglish (US)
Pages (from-to)253-262
Number of pages10
JournalCarbohydrate Research
Volume307
Issue number3-4
DOIs
StatePublished - Feb 1 1998

Fingerprint

Glyceric Acids
Pentoses
Hexoses
Xylose
Sorbose
Oxidation
Galactose
Sugars
Kinetics
Acids
Ionic strength
Stoichiometry
Osmolar Concentration
Reaction rates
Protons
Chlorides
Ions
Equipment and Supplies
chloramine-T
erythrose

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

Rangappa, Kanchugarakoppal S. ; Manjunathaswamy, Huchappa ; Raghavendra, Manikanahally P. ; Gowda, Channe. / Oxidation of threose-series pentoses and hexoses by sodium N-chloro-p- toluenesulfonamide. In: Carbohydrate Research. 1998 ; Vol. 307, No. 3-4. pp. 253-262.
@article{aa91b76f7b354af3b1ed03ffd5e532a9,
title = "Oxidation of threose-series pentoses and hexoses by sodium N-chloro-p- toluenesulfonamide",
abstract = "The kinetics and mechanism of oxidation of threose-series hexoses and pentoses by chloramine-T in alkaline medium was investigated. Kinetic studies with D-galactose, D-sorbose, D-xylose, and D-lyxose showed that the rate of the reaction was first order with respect to sugar and chloramine-T, and second order with respect to hydroxide ion. p-Toluenesulfonamide and chloride ions, the reduced products of chloramine-T, have no effect on the reaction rate. The rate increases with increase in ionic strength of the medium, and the dielectric effect is negative. Proton inventory studies in H2O-D2O mixtures suggested a single transition state. Product analysis for D-gulose, Didose, L-sorbose, D-galactose, D-talose, D-tagatose, D-xylose, and D-lyxose revealed that all lyxoseseries hexoses gave mainly mixtures of lyxonic and threonic acids with minor proportions of hexonic, xylonic and glyceric acids, whereas all xylose-series hexoses gave mixtures of lyxonic, threonic and glyceric acids with minor amounts of xylonic and hexonic acids. Xylose and lyxose gave mixtures consisting mainly of lyxonic, threonic, and glyceric acids with minor proportions of xylonic acid. From the results of kinetic studies, reaction stoichiometry, and product analysis, a possible mechanism for the oxidation of threose-series sugars with chloramine-T is suggested.",
author = "Rangappa, {Kanchugarakoppal S.} and Huchappa Manjunathaswamy and Raghavendra, {Manikanahally P.} and Channe Gowda",
year = "1998",
month = "2",
day = "1",
doi = "10.1016/S0008-6215(98)00046-9",
language = "English (US)",
volume = "307",
pages = "253--262",
journal = "Carbohydrate Research",
issn = "0008-6215",
publisher = "Elsevier BV",
number = "3-4",

}

Oxidation of threose-series pentoses and hexoses by sodium N-chloro-p- toluenesulfonamide. / Rangappa, Kanchugarakoppal S.; Manjunathaswamy, Huchappa; Raghavendra, Manikanahally P.; Gowda, Channe.

In: Carbohydrate Research, Vol. 307, No. 3-4, 01.02.1998, p. 253-262.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Oxidation of threose-series pentoses and hexoses by sodium N-chloro-p- toluenesulfonamide

AU - Rangappa, Kanchugarakoppal S.

AU - Manjunathaswamy, Huchappa

AU - Raghavendra, Manikanahally P.

AU - Gowda, Channe

PY - 1998/2/1

Y1 - 1998/2/1

N2 - The kinetics and mechanism of oxidation of threose-series hexoses and pentoses by chloramine-T in alkaline medium was investigated. Kinetic studies with D-galactose, D-sorbose, D-xylose, and D-lyxose showed that the rate of the reaction was first order with respect to sugar and chloramine-T, and second order with respect to hydroxide ion. p-Toluenesulfonamide and chloride ions, the reduced products of chloramine-T, have no effect on the reaction rate. The rate increases with increase in ionic strength of the medium, and the dielectric effect is negative. Proton inventory studies in H2O-D2O mixtures suggested a single transition state. Product analysis for D-gulose, Didose, L-sorbose, D-galactose, D-talose, D-tagatose, D-xylose, and D-lyxose revealed that all lyxoseseries hexoses gave mainly mixtures of lyxonic and threonic acids with minor proportions of hexonic, xylonic and glyceric acids, whereas all xylose-series hexoses gave mixtures of lyxonic, threonic and glyceric acids with minor amounts of xylonic and hexonic acids. Xylose and lyxose gave mixtures consisting mainly of lyxonic, threonic, and glyceric acids with minor proportions of xylonic acid. From the results of kinetic studies, reaction stoichiometry, and product analysis, a possible mechanism for the oxidation of threose-series sugars with chloramine-T is suggested.

AB - The kinetics and mechanism of oxidation of threose-series hexoses and pentoses by chloramine-T in alkaline medium was investigated. Kinetic studies with D-galactose, D-sorbose, D-xylose, and D-lyxose showed that the rate of the reaction was first order with respect to sugar and chloramine-T, and second order with respect to hydroxide ion. p-Toluenesulfonamide and chloride ions, the reduced products of chloramine-T, have no effect on the reaction rate. The rate increases with increase in ionic strength of the medium, and the dielectric effect is negative. Proton inventory studies in H2O-D2O mixtures suggested a single transition state. Product analysis for D-gulose, Didose, L-sorbose, D-galactose, D-talose, D-tagatose, D-xylose, and D-lyxose revealed that all lyxoseseries hexoses gave mainly mixtures of lyxonic and threonic acids with minor proportions of hexonic, xylonic and glyceric acids, whereas all xylose-series hexoses gave mixtures of lyxonic, threonic and glyceric acids with minor amounts of xylonic and hexonic acids. Xylose and lyxose gave mixtures consisting mainly of lyxonic, threonic, and glyceric acids with minor proportions of xylonic acid. From the results of kinetic studies, reaction stoichiometry, and product analysis, a possible mechanism for the oxidation of threose-series sugars with chloramine-T is suggested.

UR - http://www.scopus.com/inward/record.url?scp=0032004131&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032004131&partnerID=8YFLogxK

U2 - 10.1016/S0008-6215(98)00046-9

DO - 10.1016/S0008-6215(98)00046-9

M3 - Article

AN - SCOPUS:0032004131

VL - 307

SP - 253

EP - 262

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 3-4

ER -