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Title: Synthesis of montbretin A analogues yields potent competitive inhibitors of human pancreatic α-amylase

Abstract

Simplified analogues of montbretin A bind similarly to human alpha amylase and with nanomolar affinity.

Authors:
 [1];  [2];  [1];  [1];  [2]; ORCiD logo [1]
  1. Department of Chemistry, University of British Columbia, Vancouver BC, Canada V6T 1Z1
  2. Department of Biochemistry and Molecular Biology, University of British Columbia, Vancouver BC, Canada V6T 1Z3
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1572100
Resource Type:
Published Article
Journal Name:
Chemical Science
Additional Journal Information:
Journal Name: Chemical Science Journal Volume: 10 Journal Issue: 48; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Tysoe, Christina R., Caner, Sami, Calvert, Matthew B., Win-Mason, Anna, Brayer, Gary D., and Withers, Stephen G. Synthesis of montbretin A analogues yields potent competitive inhibitors of human pancreatic α-amylase. United Kingdom: N. p., 2019. Web. doi:10.1039/C9SC02610J.
Tysoe, Christina R., Caner, Sami, Calvert, Matthew B., Win-Mason, Anna, Brayer, Gary D., & Withers, Stephen G. Synthesis of montbretin A analogues yields potent competitive inhibitors of human pancreatic α-amylase. United Kingdom. doi:10.1039/C9SC02610J.
Tysoe, Christina R., Caner, Sami, Calvert, Matthew B., Win-Mason, Anna, Brayer, Gary D., and Withers, Stephen G. Wed . "Synthesis of montbretin A analogues yields potent competitive inhibitors of human pancreatic α-amylase". United Kingdom. doi:10.1039/C9SC02610J.
@article{osti_1572100,
title = {Synthesis of montbretin A analogues yields potent competitive inhibitors of human pancreatic α-amylase},
author = {Tysoe, Christina R. and Caner, Sami and Calvert, Matthew B. and Win-Mason, Anna and Brayer, Gary D. and Withers, Stephen G.},
abstractNote = {Simplified analogues of montbretin A bind similarly to human alpha amylase and with nanomolar affinity.},
doi = {10.1039/C9SC02610J},
journal = {Chemical Science},
number = 48,
volume = 10,
place = {United Kingdom},
year = {2019},
month = {12}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1039/C9SC02610J

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Works referenced in this record:

The clinical consequences of sucrase-isomaltase deficiency
journal, February 2016


Discovering novel quercetin-3-O-amino acid-esters as a new class of Src tyrosine kinase inhibitors
journal, May 2009


Efficacy of voglibose in type 2 diabetes
journal, April 2014


Acarbose-associated hepatotoxicity
journal, November 1998


Preparation of pentafluorophenyl esters of FMOC protected amino acids with pentafluorophenyl trifluoroacetate
journal, January 1990


The amylase inhibitor montbretin A reveals a new glycosidase inhibition motif
journal, July 2015

  • Williams, Leslie K.; Zhang, Xiaohua; Caner, Sami
  • Nature Chemical Biology, Vol. 11, Issue 9
  • DOI: 10.1038/nchembio.1865

In Situ Extension as an Approach for Identifying Novel α-Amylase Inhibitors
journal, August 2004

  • Numao, Shin; Damager, Iben; Li, Chunmin
  • Journal of Biological Chemistry, Vol. 279, Issue 46
  • DOI: 10.1074/jbc.M406804200

Iminosugars past, present and future: medicines for tomorrow
journal, February 2011


Glucose lowering effect of montbretin A in Zucker Diabetic Fatty rats
journal, November 2015

  • Yuen, Violet G.; Coleman, John; Withers, Steven G.
  • Molecular and Cellular Biochemistry, Vol. 411, Issue 1-2
  • DOI: 10.1007/s11010-015-2599-4

An Update on the Etiology and Epidemiology of Diabetes Mellitus
journal, November 2006

  • Adeghate, E.; Schattner, P.; Dunn, E.
  • Annals of the New York Academy of Sciences, Vol. 1084, Issue 1
  • DOI: 10.1196/annals.1372.029

Miglitol: A Review of its Therapeutic Potential in Type 2 Diabetes Mellitus
journal, January 2000


Acarbose Improves Glycemic Control in Overweight Type 2 Diabetic Patients Insufficiently Treated With Metformin
journal, February 2003


Flavonoids for Controlling Starch Digestion: Structural Requirements for Inhibiting Human α-Amylase
journal, June 2008

  • Lo Piparo, Elena; Scheib, Holger; Frei, Nathalie
  • Journal of Medicinal Chemistry, Vol. 51, Issue 12
  • DOI: 10.1021/jm800115x

Cloning, mutagenesis, and structural analysis of human pancreatic α-amylase expressed in pichia pastoris
journal, January 1999

  • Rydberg, Edwin H.; Sidhu, Gary; Vo, Hung C.
  • Protein Science, Vol. 8, Issue 3
  • DOI: 10.1110/ps.8.3.635

Postprandial hyperglycaemia and α-glucosidase inhibitors
journal, July 1998


The structure of human pancreatic α -amylase at 1.8 Å resolution and comparisons with related enzymes
journal, September 1995

  • Brayer, Gary D.; Luo, Yaoguang; Withers, Stephen G.
  • Protein Science, Vol. 4, Issue 9
  • DOI: 10.1002/pro.5560040908

Subsite Mapping of the Human Pancreatic α-Amylase Active Site through Structural, Kinetic, and Mutagenesis Techniques ,
journal, April 2000

  • Brayer, Gary D.; Sidhu, Gary; Maurus, Robert
  • Biochemistry, Vol. 39, Issue 16
  • DOI: 10.1021/bi9921182

The Role of Acarbose in the Treatment of Non–Insulin-Dependent Diabetes Mellitus
journal, July 1998


Inhibition of .ALPHA.-Glucosidase and .ALPHA.-Amylase by Flavonoids
journal, January 2006

  • Tadera, Kenjiro; Minami, Yuji; Takamatsu, Kouta
  • Journal of Nutritional Science and Vitaminology, Vol. 52, Issue 2
  • DOI: 10.3177/jnsv.52.149