Synthesis of α- and β-D-glucopyranuronate 1-phosphate and α-D-glucopyranuronate 1-fluoride: intermediates in the synthesis of D-glucuronic acid from starch

André Heeres, Henk A. Van Doren, Kees F. Gotlieb, Ido Pieter Bleeker

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

The title uronates were prepared by 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) catalysed sodium hypochlorite oxidation of α- and β-D-glucopyranosylphosphate (α-/β-Glc-1-P) and α-D-glucopyranosyl fluoride (α-Glc-1-F). Quantitative recovery of the TEMPO catalyst was achieved by azeotropic distillation of a small part of the reaction mixture. Also, a heterogeneous catalyst system was prepared by immobilisation of 4-oxo-tetramethyl-1-piperidinyloxy (OTEMPO) on amino-functionalized silica. The protected uronates were hydrolysed to yield D-glucuronate. Since α- and β-Glc-1-P and α-Glc-1-F can be obtained from starch in one step, D-glucuronic acid is now available from starch in a convenient three-step sequence.
Original languageEnglish
Pages (from-to)221-227
JournalCarbohydrate research
Volume299
Issue number4
DOIs
Publication statusPublished - 30 Apr 1997

Keywords

  • catalyst immobilization
  • d-glucuronic acid
  • naocl-tmepo oxidation
  • α-d-glucopyranuronate 1-fluoride
  • α-d-glucopyranuronate 1-phosphate
  • β-d-glucopyranuronate 1-phosphate

Cite this

@article{5ab858362391454990cef978978127c5,
title = "Synthesis of α- and β-D-glucopyranuronate 1-phosphate and α-D-glucopyranuronate 1-fluoride: intermediates in the synthesis of D-glucuronic acid from starch",
abstract = "The title uronates were prepared by 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) catalysed sodium hypochlorite oxidation of α- and β-D-glucopyranosylphosphate (α-/β-Glc-1-P) and α-D-glucopyranosyl fluoride (α-Glc-1-F). Quantitative recovery of the TEMPO catalyst was achieved by azeotropic distillation of a small part of the reaction mixture. Also, a heterogeneous catalyst system was prepared by immobilisation of 4-oxo-tetramethyl-1-piperidinyloxy (OTEMPO) on amino-functionalized silica. The protected uronates were hydrolysed to yield D-glucuronate. Since α- and β-Glc-1-P and α-Glc-1-F can be obtained from starch in one step, D-glucuronic acid is now available from starch in a convenient three-step sequence.",
keywords = "catalyst immobilization, d-glucuronic acid, naocl-tmepo oxidation, α-d-glucopyranuronate 1-fluoride, α-d-glucopyranuronate 1-phosphate, β-d-glucopyranuronate 1-phosphate",
author = "Andr{\'e} Heeres and {Van Doren}, {Henk A.} and Gotlieb, {Kees F.} and Bleeker, {Ido Pieter}",
year = "1997",
month = "4",
day = "30",
doi = "10.1016/S0008-6215(97)00030-X",
language = "English",
volume = "299",
pages = "221--227",
journal = "Carbohydrate research",
issn = "0008-6215",
publisher = "Elsevier",
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Synthesis of α- and β-D-glucopyranuronate 1-phosphate and α-D-glucopyranuronate 1-fluoride: intermediates in the synthesis of D-glucuronic acid from starch. / Heeres, André; Van Doren, Henk A.; Gotlieb, Kees F.; Bleeker, Ido Pieter.

In: Carbohydrate research, Vol. 299, No. 4, 30.04.1997, p. 221-227.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Synthesis of α- and β-D-glucopyranuronate 1-phosphate and α-D-glucopyranuronate 1-fluoride: intermediates in the synthesis of D-glucuronic acid from starch

AU - Heeres, André

AU - Van Doren, Henk A.

AU - Gotlieb, Kees F.

AU - Bleeker, Ido Pieter

PY - 1997/4/30

Y1 - 1997/4/30

N2 - The title uronates were prepared by 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) catalysed sodium hypochlorite oxidation of α- and β-D-glucopyranosylphosphate (α-/β-Glc-1-P) and α-D-glucopyranosyl fluoride (α-Glc-1-F). Quantitative recovery of the TEMPO catalyst was achieved by azeotropic distillation of a small part of the reaction mixture. Also, a heterogeneous catalyst system was prepared by immobilisation of 4-oxo-tetramethyl-1-piperidinyloxy (OTEMPO) on amino-functionalized silica. The protected uronates were hydrolysed to yield D-glucuronate. Since α- and β-Glc-1-P and α-Glc-1-F can be obtained from starch in one step, D-glucuronic acid is now available from starch in a convenient three-step sequence.

AB - The title uronates were prepared by 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) catalysed sodium hypochlorite oxidation of α- and β-D-glucopyranosylphosphate (α-/β-Glc-1-P) and α-D-glucopyranosyl fluoride (α-Glc-1-F). Quantitative recovery of the TEMPO catalyst was achieved by azeotropic distillation of a small part of the reaction mixture. Also, a heterogeneous catalyst system was prepared by immobilisation of 4-oxo-tetramethyl-1-piperidinyloxy (OTEMPO) on amino-functionalized silica. The protected uronates were hydrolysed to yield D-glucuronate. Since α- and β-Glc-1-P and α-Glc-1-F can be obtained from starch in one step, D-glucuronic acid is now available from starch in a convenient three-step sequence.

KW - catalyst immobilization

KW - d-glucuronic acid

KW - naocl-tmepo oxidation

KW - α-d-glucopyranuronate 1-fluoride

KW - α-d-glucopyranuronate 1-phosphate

KW - β-d-glucopyranuronate 1-phosphate

U2 - 10.1016/S0008-6215(97)00030-X

DO - 10.1016/S0008-6215(97)00030-X

M3 - Article

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