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Transglycosylation reactions of Bacillus stearothermophilus maltogenic amylase with acarbose and various acceptors

Abstract

It was observed that Bacillus stearothermophilus maltogenic amylase cleaved the first glycosidic bond of acarbose to produce glucose and a pseudotrisaccharide (PTS) that was transferred to C-6 of the glucose to give an {alpha}-(1-6) glycosidic linkage and the formation of isoacarbose. The addition of a number of different carbohydrates to the digest gave transfer products in which PTS was primarily attached {alpha}-(1-6) to d-glucose, d-mannose, d-galactose, and methyl {alpha}-d-glucopyranoside. With d-fructopyranose and d-xylopyranose, PTS was linked {alpha}-(1-5) and {alpha}-(1-4), respectively. PTS was primarily transferred to C-6 of the nonreducing residue of maltose, cellobiose, lactose, and gentiobiose. Lesser amounts of {alpha}-(1-3) and/or {alpha}-(1-4) transfer products were also observed for these carbohydrate acceptors. The major transfer product to sucrose gave PTS linked {alpha}-(1-4) to the glucose residue. {alpha},{alpha}-Trehalose gave two major products with PTS linked {alpha}-(1-6) and {alpha}-(1-4). Maltitol gave two major products with PTS linked {alpha}-(1-6) and {alpha}-(1-4) to the glucopyranose residue. Raffinose gave two major products with PTS linked {alpha}-(1-6) and {alpha}-(1-4) to the d-galactopyranose residue. Maltotriose gave two major products with PTS linked {alpha}-(1-6) and {alpha}-(1-4) to the nonreducing end glucopyranose residue. Xylitol gave PTS linked {alpha}-(1-5) as the major product and d-glucitol gave PTS linked {alpha}-(1-6) as the  More>>
Authors:
Hwa Park, K; Jeong Kim, M; Seob Lee, H; Kim, D; [1]  Soo Han, N; Robyt, J F [2] 
  1. Department of Food Science and Technology and Research Center for New Bio-Materials in Agriculture, Seoul National University, Suwon (Korea, Republic of)
  2. Laboratory for Carbohydrate Chemistry and Enzymology, Department of Biochemistry and Biophysics, Iowa State University, Ames, IA (United States)
Publication Date:
Dec 15, 1998
Product Type:
Journal Article
Reference Number:
EDB-01:003927
Resource Relation:
Journal Name: Carbohydrate Research; Journal Volume: 313; Journal Issue: 3-4; Other Information: Country of input: IAEA; PBD: 15 Dec 1998
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; ION EXCHANGE CHROMATOGRAPHY; OLIGOSACCHARIDES; OPTICAL ACTIVITY; STEREOCHEMISTRY; STRUCTURAL CHEMICAL ANALYSIS; THIN-LAYER CHROMATOGRAPHY
OSTI ID:
20121464
Country of Origin:
Netherlands
Language:
English
Other Identifying Numbers:
Journal ID: ISSN 0008-6215; CRBRAT; TRN: NL99$0051061636
Submitting Site:
NLN
Size:
page(s) 235-246
Announcement Date:

Citation Formats

Hwa Park, K, Jeong Kim, M, Seob Lee, H, Kim, D, Soo Han, N, and Robyt, J F. Transglycosylation reactions of Bacillus stearothermophilus maltogenic amylase with acarbose and various acceptors. Netherlands: N. p., 1998. Web. doi:10.1016/S0008-6215(98)00276-6.
Hwa Park, K, Jeong Kim, M, Seob Lee, H, Kim, D, Soo Han, N, & Robyt, J F. Transglycosylation reactions of Bacillus stearothermophilus maltogenic amylase with acarbose and various acceptors. Netherlands. doi:10.1016/S0008-6215(98)00276-6.
Hwa Park, K, Jeong Kim, M, Seob Lee, H, Kim, D, Soo Han, N, and Robyt, J F. 1998. "Transglycosylation reactions of Bacillus stearothermophilus maltogenic amylase with acarbose and various acceptors." Netherlands. doi:10.1016/S0008-6215(98)00276-6. https://www.osti.gov/servlets/purl/10.1016/S0008-6215(98)00276-6.
@misc{etde_20121464,
title = {Transglycosylation reactions of Bacillus stearothermophilus maltogenic amylase with acarbose and various acceptors}
author = {Hwa Park, K, Jeong Kim, M, Seob Lee, H, Kim, D, Soo Han, N, and Robyt, J F}
abstractNote = {It was observed that Bacillus stearothermophilus maltogenic amylase cleaved the first glycosidic bond of acarbose to produce glucose and a pseudotrisaccharide (PTS) that was transferred to C-6 of the glucose to give an {alpha}-(1-6) glycosidic linkage and the formation of isoacarbose. The addition of a number of different carbohydrates to the digest gave transfer products in which PTS was primarily attached {alpha}-(1-6) to d-glucose, d-mannose, d-galactose, and methyl {alpha}-d-glucopyranoside. With d-fructopyranose and d-xylopyranose, PTS was linked {alpha}-(1-5) and {alpha}-(1-4), respectively. PTS was primarily transferred to C-6 of the nonreducing residue of maltose, cellobiose, lactose, and gentiobiose. Lesser amounts of {alpha}-(1-3) and/or {alpha}-(1-4) transfer products were also observed for these carbohydrate acceptors. The major transfer product to sucrose gave PTS linked {alpha}-(1-4) to the glucose residue. {alpha},{alpha}-Trehalose gave two major products with PTS linked {alpha}-(1-6) and {alpha}-(1-4). Maltitol gave two major products with PTS linked {alpha}-(1-6) and {alpha}-(1-4) to the glucopyranose residue. Raffinose gave two major products with PTS linked {alpha}-(1-6) and {alpha}-(1-4) to the d-galactopyranose residue. Maltotriose gave two major products with PTS linked {alpha}-(1-6) and {alpha}-(1-4) to the nonreducing end glucopyranose residue. Xylitol gave PTS linked {alpha}-(1-5) as the major product and d-glucitol gave PTS linked {alpha}-(1-6) as the only product. The structures of the transfer products were determined using thin layer-chromatography, high-performance ion chromatography, enzyme hydrolysis, methylation analysis and {sup 13}C NMR spectroscopy. The best acceptor was gentiobiose, followed closely by maltose and cellobiose, and the weakest acceptor was d-glucitol. (Copyright (c) 1998 Elsevier Science B.V., Amsterdam. All rights reserved.)}
doi = {10.1016/S0008-6215(98)00276-6}
journal = {Carbohydrate Research}
issue = {3-4}
volume = {313}
journal type = {AC}
place = {Netherlands}
year = {1998}
month = {Dec}
}