The synthesis and glycosidase inhibitory activity of analogues of tiruchanduramine

Zackary J.R. Ashworth; Barbara Bartholomew; Daniel M. Evans; Josephine Forde-Thomas; Karl F. Hoffmann; Reece Murdoch; Robert J. Nash; Hazel Sharp; Helen Whiteland; Patrick J. Murphy

doi:10.3987/COM-20-14236

The synthesis and glycosidase inhibitory activity of analogues of tiruchanduramine

Zackary J.R. Ashworth, Barbara Bartholomew, Daniel M. Evans, Josephine Forde-Thomas, Karl F. Hoffmann, Reece Murdoch, Robert J. Nash, Hazel Sharp, Helen Whiteland, Patrick J. Murphy^*

^*Corresponding author for this work

Department of Life Sciences

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

Five analogues (7a-e) of the metabolite tiruchanduramine 1 were prepared. Compounds 7d and 7e were specific inhibitors of yeast α-glucosidase, whilst 7e specifically inhibited Bacillus α-glucosidase. Compounds 7b and 7c were the best inhibitors of β-glucosidase. All 5 compounds inhibited β-galactosidase, but once again 7e was the best inhibitor. It was apparent that different chain lengths in the compounds 7a-e affect the degree of inhibition. Some of the synthetic analogues show significantly improved inhibition of α-glucosidases when compared to tiruchanduramine 1 and also improved specificity.

Original language	English
Pages (from-to)	609-621
Number of pages	13
Journal	Heterocycles
Volume	100
Issue number	4
DOIs	https://doi.org/10.3987/COM-20-14236
Publication status	Published - 19 Mar 2020

Access to Document

10.3987/COM-20-14236

Permanent link

Persistent link

Cite this

@article{b5c5fd7ea1974abea556ee097bccecc9,

title = "The synthesis and glycosidase inhibitory activity of analogues of tiruchanduramine",

abstract = "Five analogues (7a-e) of the metabolite tiruchanduramine 1 were prepared. Compounds 7d and 7e were specific inhibitors of yeast α-glucosidase, whilst 7e specifically inhibited Bacillus α-glucosidase. Compounds 7b and 7c were the best inhibitors of β-glucosidase. All 5 compounds inhibited β-galactosidase, but once again 7e was the best inhibitor. It was apparent that different chain lengths in the compounds 7a-e affect the degree of inhibition. Some of the synthetic analogues show significantly improved inhibition of α-glucosidases when compared to tiruchanduramine 1 and also improved specificity.",

author = "Ashworth, \{Zackary J.R.\} and Barbara Bartholomew and Evans, \{Daniel M.\} and Josephine Forde-Thomas and Hoffmann, \{Karl F.\} and Reece Murdoch and Nash, \{Robert J.\} and Hazel Sharp and Helen Whiteland and Murphy, \{Patrick J.\}",

year = "2020",

month = mar,

day = "19",

doi = "10.3987/COM-20-14236",

language = "English",

volume = "100",

pages = "609--621",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "4",

}

TY - JOUR

T1 - The synthesis and glycosidase inhibitory activity of analogues of tiruchanduramine

AU - Ashworth, Zackary J.R.

AU - Bartholomew, Barbara

AU - Evans, Daniel M.

AU - Forde-Thomas, Josephine

AU - Hoffmann, Karl F.

AU - Murdoch, Reece

AU - Nash, Robert J.

AU - Sharp, Hazel

AU - Whiteland, Helen

AU - Murphy, Patrick J.

PY - 2020/3/19

Y1 - 2020/3/19

N2 - Five analogues (7a-e) of the metabolite tiruchanduramine 1 were prepared. Compounds 7d and 7e were specific inhibitors of yeast α-glucosidase, whilst 7e specifically inhibited Bacillus α-glucosidase. Compounds 7b and 7c were the best inhibitors of β-glucosidase. All 5 compounds inhibited β-galactosidase, but once again 7e was the best inhibitor. It was apparent that different chain lengths in the compounds 7a-e affect the degree of inhibition. Some of the synthetic analogues show significantly improved inhibition of α-glucosidases when compared to tiruchanduramine 1 and also improved specificity.

AB - Five analogues (7a-e) of the metabolite tiruchanduramine 1 were prepared. Compounds 7d and 7e were specific inhibitors of yeast α-glucosidase, whilst 7e specifically inhibited Bacillus α-glucosidase. Compounds 7b and 7c were the best inhibitors of β-glucosidase. All 5 compounds inhibited β-galactosidase, but once again 7e was the best inhibitor. It was apparent that different chain lengths in the compounds 7a-e affect the degree of inhibition. Some of the synthetic analogues show significantly improved inhibition of α-glucosidases when compared to tiruchanduramine 1 and also improved specificity.

UR - http://www.scopus.com/inward/record.url?scp=85085469306&partnerID=8YFLogxK

U2 - 10.3987/COM-20-14236

DO - 10.3987/COM-20-14236

M3 - Article

AN - SCOPUS:85085469306

SN - 0385-5414

VL - 100

SP - 609

EP - 621

JO - Heterocycles

JF - Heterocycles

IS - 4

ER -

The synthesis and glycosidase inhibitory activity of analogues of tiruchanduramine

Abstract

Access to Document

Permanent link

Other files and links

Fingerprint

Cite this