Chemoenzymatic preparation of 2-chloro-4-nitrophenyl β-maltooligosaccharide glycosides using glycogen phosphorylase b

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

In the present work, we aimed to develop a new chemoenzymatic procedure for the synthesis of β-maltooligosaccharide glycosides. The primer in the enzymatic reaction was 2-chloro-4-nitrophenyl β-maltoheptaoside (G7-CNP), which was synthesised from β-cyclodextrin (β-CD) using a very convenient chemical method [E. Farkas, L. Janossy, J. Harangi, L. Kandra, A. Liptak, Carbohydr. Res., 303 (1997) 407-415]. Shorter chain length CNP-maltooligosaccharides in the range of dp 3-6 were prepared using rabbit skeletal muscle glycogen phosphorylase b (EC 2.4.1.1). Detailed enzymological investigations revealed that the conversion of G7-CNP was highly dependent on the conditions of phosphorolysis. A 100% conversion of G7-CNP was achieved during 10 min in 1 M phosphate buffer (pH 6.8) at 30°C with the tetramer glycoside (77%) as the main product. Phosphorolysis at 10°C for 10 min resulted in 89% conversion and G4-, G5-, and G6-CNP oligomers were detected in the ratio of 29:26:34%, respectively. The reaction pattern was investigated using an HPLC system. The preparative scale isolation of G(3→6)-CNP glycosides was achieved by size-exclusion column chromatography (SEC) on Toyopearl HW-40 matrix. The productivity of the synthesis was improved by yields of up to 70-75%. Copyright (C) 1999 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)180-186
Number of pages7
JournalCarbohydrate Research
Volume315
Issue number1-2
DOIs
Publication statusPublished - Jan 31 1999

Fingerprint

Phosphorylase b
Glycogen Phosphorylase
Glycosides
Column chromatography
Size exclusion chromatography
Cyclodextrins
Chain length
Oligomers
Gel Chromatography
Muscle
Buffers
Skeletal Muscle
Productivity
Phosphates
High Pressure Liquid Chromatography
Rabbits
4-nitrophenyl
maltooligosaccharides

Keywords

  • Glycogen phosphorylase b
  • Maltooligosaccharide series
  • Size-exclusion column chromatography

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

@article{a119ad2ac191480c9304c4681ba7cb70,
title = "Chemoenzymatic preparation of 2-chloro-4-nitrophenyl β-maltooligosaccharide glycosides using glycogen phosphorylase b",
abstract = "In the present work, we aimed to develop a new chemoenzymatic procedure for the synthesis of β-maltooligosaccharide glycosides. The primer in the enzymatic reaction was 2-chloro-4-nitrophenyl β-maltoheptaoside (G7-CNP), which was synthesised from β-cyclodextrin (β-CD) using a very convenient chemical method [E. Farkas, L. Janossy, J. Harangi, L. Kandra, A. Liptak, Carbohydr. Res., 303 (1997) 407-415]. Shorter chain length CNP-maltooligosaccharides in the range of dp 3-6 were prepared using rabbit skeletal muscle glycogen phosphorylase b (EC 2.4.1.1). Detailed enzymological investigations revealed that the conversion of G7-CNP was highly dependent on the conditions of phosphorolysis. A 100{\%} conversion of G7-CNP was achieved during 10 min in 1 M phosphate buffer (pH 6.8) at 30°C with the tetramer glycoside (77{\%}) as the main product. Phosphorolysis at 10°C for 10 min resulted in 89{\%} conversion and G4-, G5-, and G6-CNP oligomers were detected in the ratio of 29:26:34{\%}, respectively. The reaction pattern was investigated using an HPLC system. The preparative scale isolation of G(3→6)-CNP glycosides was achieved by size-exclusion column chromatography (SEC) on Toyopearl HW-40 matrix. The productivity of the synthesis was improved by yields of up to 70-75{\%}. Copyright (C) 1999 Elsevier Science Ltd.",
keywords = "Glycogen phosphorylase b, Maltooligosaccharide series, Size-exclusion column chromatography",
author = "L. Kandra and G. Gy{\'e}m{\'a}nt and A. Lipt{\'a}k",
year = "1999",
month = "1",
day = "31",
doi = "10.1016/S0008-6215(98)00324-3",
language = "English",
volume = "315",
pages = "180--186",
journal = "Carbohydrate Research",
issn = "0008-6215",
publisher = "Elsevier BV",
number = "1-2",

}

TY - JOUR

T1 - Chemoenzymatic preparation of 2-chloro-4-nitrophenyl β-maltooligosaccharide glycosides using glycogen phosphorylase b

AU - Kandra, L.

AU - Gyémánt, G.

AU - Lipták, A.

PY - 1999/1/31

Y1 - 1999/1/31

N2 - In the present work, we aimed to develop a new chemoenzymatic procedure for the synthesis of β-maltooligosaccharide glycosides. The primer in the enzymatic reaction was 2-chloro-4-nitrophenyl β-maltoheptaoside (G7-CNP), which was synthesised from β-cyclodextrin (β-CD) using a very convenient chemical method [E. Farkas, L. Janossy, J. Harangi, L. Kandra, A. Liptak, Carbohydr. Res., 303 (1997) 407-415]. Shorter chain length CNP-maltooligosaccharides in the range of dp 3-6 were prepared using rabbit skeletal muscle glycogen phosphorylase b (EC 2.4.1.1). Detailed enzymological investigations revealed that the conversion of G7-CNP was highly dependent on the conditions of phosphorolysis. A 100% conversion of G7-CNP was achieved during 10 min in 1 M phosphate buffer (pH 6.8) at 30°C with the tetramer glycoside (77%) as the main product. Phosphorolysis at 10°C for 10 min resulted in 89% conversion and G4-, G5-, and G6-CNP oligomers were detected in the ratio of 29:26:34%, respectively. The reaction pattern was investigated using an HPLC system. The preparative scale isolation of G(3→6)-CNP glycosides was achieved by size-exclusion column chromatography (SEC) on Toyopearl HW-40 matrix. The productivity of the synthesis was improved by yields of up to 70-75%. Copyright (C) 1999 Elsevier Science Ltd.

AB - In the present work, we aimed to develop a new chemoenzymatic procedure for the synthesis of β-maltooligosaccharide glycosides. The primer in the enzymatic reaction was 2-chloro-4-nitrophenyl β-maltoheptaoside (G7-CNP), which was synthesised from β-cyclodextrin (β-CD) using a very convenient chemical method [E. Farkas, L. Janossy, J. Harangi, L. Kandra, A. Liptak, Carbohydr. Res., 303 (1997) 407-415]. Shorter chain length CNP-maltooligosaccharides in the range of dp 3-6 were prepared using rabbit skeletal muscle glycogen phosphorylase b (EC 2.4.1.1). Detailed enzymological investigations revealed that the conversion of G7-CNP was highly dependent on the conditions of phosphorolysis. A 100% conversion of G7-CNP was achieved during 10 min in 1 M phosphate buffer (pH 6.8) at 30°C with the tetramer glycoside (77%) as the main product. Phosphorolysis at 10°C for 10 min resulted in 89% conversion and G4-, G5-, and G6-CNP oligomers were detected in the ratio of 29:26:34%, respectively. The reaction pattern was investigated using an HPLC system. The preparative scale isolation of G(3→6)-CNP glycosides was achieved by size-exclusion column chromatography (SEC) on Toyopearl HW-40 matrix. The productivity of the synthesis was improved by yields of up to 70-75%. Copyright (C) 1999 Elsevier Science Ltd.

KW - Glycogen phosphorylase b

KW - Maltooligosaccharide series

KW - Size-exclusion column chromatography

UR - http://www.scopus.com/inward/record.url?scp=0344348934&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0344348934&partnerID=8YFLogxK

U2 - 10.1016/S0008-6215(98)00324-3

DO - 10.1016/S0008-6215(98)00324-3

M3 - Article

VL - 315

SP - 180

EP - 186

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 1-2

ER -