The synthesis of novel chromogenic enzyme substrates for detection of bacterial glycosidases and their applications in diagnostic microbiology

Michael Burton; John D. Perry; Stephen P. Stanforth; Hayley J. Turner

doi:10.1016/j.bmc.2018.08.023

The synthesis of novel chromogenic enzyme substrates for detection of bacterial glycosidases and their applications in diagnostic microbiology

Michael Burton, John D. Perry, Stephen P. Stanforth, Hayley J. Turner

Applied Sciences Department

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Abstract

The preparation and evaluation of chromogenic substrates for detecting bacterial glycosidase enzymes is reported. These substrates are monoglycoside derivatives of the metal chelators catechol, 2,3-dihydroxynaphthalene (DHN) and 6,7-dibromo-2,3-dihydroxynaphthalene (6,7-dibromo-DHN). When hydrolysed by appropriate bacterial enzymes these substrates produced coloured chelates in the presence of ammonium iron(III) citrate, thus enabling bacterial detection. A β-D-riboside of DHN and a β-D-glucuronide derivative of 6,7-dibromo-DHN were particularly effective for the detection of S. aureus and E. coli respectively.

Original language	English
Pages (from-to)	4841-4849
Number of pages	9
Journal	Bioorganic & Medicinal Chemistry
Volume	26
Issue number	17
Early online date	17 Aug 2018
DOIs	https://doi.org/10.1016/j.bmc.2018.08.023
Publication status	Published - 15 Sept 2018

Keywords

Enzyme substrates
Chromogenic substrates
Glycosidase
Pathogenic microorganisms
Bacterial detection

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10.1016/j.bmc.2018.08.023

Burton et al - The synthesis of novel chromogenic enzyme substrates for detection of bacterial glycosidases and their applications in diagnostic microbiology AAMAccepted author manuscript, 1.49 MB

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title = "The synthesis of novel chromogenic enzyme substrates for detection of bacterial glycosidases and their applications in diagnostic microbiology",

abstract = "The preparation and evaluation of chromogenic substrates for detecting bacterial glycosidase enzymes is reported. These substrates are monoglycoside derivatives of the metal chelators catechol, 2,3-dihydroxynaphthalene (DHN) and 6,7-dibromo-2,3-dihydroxynaphthalene (6,7-dibromo-DHN). When hydrolysed by appropriate bacterial enzymes these substrates produced coloured chelates in the presence of ammonium iron(III) citrate, thus enabling bacterial detection. A β-D-riboside of DHN and a β-D-glucuronide derivative of 6,7-dibromo-DHN were particularly effective for the detection of S. aureus and E. coli respectively.",

keywords = "Enzyme substrates, Chromogenic substrates, Glycosidase, Pathogenic microorganisms, Bacterial detection",

author = "Michael Burton and Perry, {John D.} and Stanforth, {Stephen P.} and Turner, {Hayley J.}",

year = "2018",

month = sep,

day = "15",

doi = "10.1016/j.bmc.2018.08.023",

language = "English",

volume = "26",

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journal = "Bioorganic & Medicinal Chemistry",

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publisher = "Elsevier",

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TY - JOUR

T1 - The synthesis of novel chromogenic enzyme substrates for detection of bacterial glycosidases and their applications in diagnostic microbiology

AU - Burton, Michael

AU - Perry, John D.

AU - Stanforth, Stephen P.

AU - Turner, Hayley J.

PY - 2018/9/15

Y1 - 2018/9/15

N2 - The preparation and evaluation of chromogenic substrates for detecting bacterial glycosidase enzymes is reported. These substrates are monoglycoside derivatives of the metal chelators catechol, 2,3-dihydroxynaphthalene (DHN) and 6,7-dibromo-2,3-dihydroxynaphthalene (6,7-dibromo-DHN). When hydrolysed by appropriate bacterial enzymes these substrates produced coloured chelates in the presence of ammonium iron(III) citrate, thus enabling bacterial detection. A β-D-riboside of DHN and a β-D-glucuronide derivative of 6,7-dibromo-DHN were particularly effective for the detection of S. aureus and E. coli respectively.

AB - The preparation and evaluation of chromogenic substrates for detecting bacterial glycosidase enzymes is reported. These substrates are monoglycoside derivatives of the metal chelators catechol, 2,3-dihydroxynaphthalene (DHN) and 6,7-dibromo-2,3-dihydroxynaphthalene (6,7-dibromo-DHN). When hydrolysed by appropriate bacterial enzymes these substrates produced coloured chelates in the presence of ammonium iron(III) citrate, thus enabling bacterial detection. A β-D-riboside of DHN and a β-D-glucuronide derivative of 6,7-dibromo-DHN were particularly effective for the detection of S. aureus and E. coli respectively.

KW - Enzyme substrates

KW - Chromogenic substrates

KW - Glycosidase

KW - Pathogenic microorganisms

KW - Bacterial detection

U2 - 10.1016/j.bmc.2018.08.023

DO - 10.1016/j.bmc.2018.08.023

M3 - Article

SN - 0968-0896

VL - 26

SP - 4841

EP - 4849

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

IS - 17

ER -

The synthesis of novel chromogenic enzyme substrates for detection of bacterial glycosidases and their applications in diagnostic microbiology

Abstract

Keywords

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