Mechanistic investigation of oxidation of 6-deoxyhexoses by sodium n-chloro-p-toluenesulfonamide in alkaline medium

K. S. Rangappa; M. P. Raghavendra; N. Anitha; Channe Gowda

Mechanistic investigation of oxidation of 6-deoxyhexoses by sodium n-chloro-p-toluenesulfonamide in alkaline medium

K. S. Rangappa, M. P. Raghavendra, N. Anitha, Channe Gowda

Department of Biochemistry and Molecular Biology

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

2 Scopus citations

Abstract

The kinetics and mechanism of oxidation of L-fucose and L-rhamnose by chloramine-T (CAT) in alkaline medium has been investigated at 40°C. The rate of the reaction is first order with respect to [sugar][CAT] and [hydroxide ion]. The reaction rate is influenced by a change in ionic strength of the medium and the dielectric effect has been found to be negative. Proton inventory studies have been made in H₂O-D₂O mixtures. Activation parameters have been determined from the Arrhenius plots, HPLC and GLC-MS analyses of the products indicate that 6-deoxyhexoses are oxidized to a mixture of aldonic acids. The proposed mechanism is consistent with the observed results.

Original language	English (US)
Pages (from-to)	836-841
Number of pages	6
Journal	Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry
Volume	39
Issue number	11
State	Published - Dec 1 2000

All Science Journal Classification (ASJC) codes

Pharmacology, Toxicology and Pharmaceutics(all)
Organic Chemistry

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title = "Mechanistic investigation of oxidation of 6-deoxyhexoses by sodium n-chloro-p-toluenesulfonamide in alkaline medium",

abstract = "The kinetics and mechanism of oxidation of L-fucose and L-rhamnose by chloramine-T (CAT) in alkaline medium has been investigated at 40°C. The rate of the reaction is first order with respect to [sugar][CAT] and [hydroxide ion]. The reaction rate is influenced by a change in ionic strength of the medium and the dielectric effect has been found to be negative. Proton inventory studies have been made in H2O-D2O mixtures. Activation parameters have been determined from the Arrhenius plots, HPLC and GLC-MS analyses of the products indicate that 6-deoxyhexoses are oxidized to a mixture of aldonic acids. The proposed mechanism is consistent with the observed results.",

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year = "2000",

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T1 - Mechanistic investigation of oxidation of 6-deoxyhexoses by sodium n-chloro-p-toluenesulfonamide in alkaline medium

AU - Rangappa, K. S.

AU - Raghavendra, M. P.

AU - Anitha, N.

AU - Gowda, Channe

PY - 2000/12/1

Y1 - 2000/12/1

N2 - The kinetics and mechanism of oxidation of L-fucose and L-rhamnose by chloramine-T (CAT) in alkaline medium has been investigated at 40°C. The rate of the reaction is first order with respect to [sugar][CAT] and [hydroxide ion]. The reaction rate is influenced by a change in ionic strength of the medium and the dielectric effect has been found to be negative. Proton inventory studies have been made in H2O-D2O mixtures. Activation parameters have been determined from the Arrhenius plots, HPLC and GLC-MS analyses of the products indicate that 6-deoxyhexoses are oxidized to a mixture of aldonic acids. The proposed mechanism is consistent with the observed results.

AB - The kinetics and mechanism of oxidation of L-fucose and L-rhamnose by chloramine-T (CAT) in alkaline medium has been investigated at 40°C. The rate of the reaction is first order with respect to [sugar][CAT] and [hydroxide ion]. The reaction rate is influenced by a change in ionic strength of the medium and the dielectric effect has been found to be negative. Proton inventory studies have been made in H2O-D2O mixtures. Activation parameters have been determined from the Arrhenius plots, HPLC and GLC-MS analyses of the products indicate that 6-deoxyhexoses are oxidized to a mixture of aldonic acids. The proposed mechanism is consistent with the observed results.

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M3 - Article

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SN - 0376-4699

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JO - Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

JF - Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

IS - 11

ER -

Mechanistic investigation of oxidation of 6-deoxyhexoses by sodium n-chloro-p-toluenesulfonamide in alkaline medium

Abstract

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