Introduction of <i>C</i>-alkyl branches to <scp>l</scp>-iminosugars changes their active site binding orientation-Reference-Cited by-同舟云学术

Introduction of C-alkyl branches to l-iminosugars changes their active site binding orientation

Published:2022 Issue:36 Volume:20 Page:7250-7260
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Kato Atsushi¹^ORCID,Nakagome Izumi²,Yoshimura Kosuke¹,Kanekiyo Uta¹,Kishida Mana¹,Shinzawa Kenta¹^ORCID,Lu Tian-Tian³⁴,Li Yi-Xian³⁴,Nash Robert J.⁵,Fleet George W. J.⁶,Tanaka Nobutada²,Yu Chu-Yi³⁴^ORCID

Affiliation:

1. Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan

2. School of Pharmaceutical Sciences, Kitasato University, Tokyo 108-8641, Japan

3. Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China

4. University of Chinese Academy of Sciences, Beijing 100049, China

5. Institute of Biological, Environmental and Rural Sciences/Phytoquest Limited, Plas Gogerddan, Aberystwyth, Ceredigion, SY23 3EB, UK

6. Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, OX1 3TA, UK

Abstract

5-C-Methyl-l-ido-DNJ showed a strong affinity for rhGAA (Ki 0.060 μM). This study provides the first example of a strategy to design high-affinity ligands by introducing alkyl branches into rare sugars and l-sugar-type iminosugars to change the orientation of binding.

Funder

Leverhulme Trust

Japan Society for the Promotion of Science

National Natural Science Foundation of China

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2022/OB/D2OB01099B

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