Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer

Manikandan Kadirvel; William T. Stimpson; Souad Moumene-Afifi; Biljana Arsic; Nicola Glynn; Nigel Halliday; Paul Williams; Peter Gilbert; Andrew J. McBain; Sally Freeman; John M. Gardiner

doi:10.1016/j.bmcl.2010.02.064

Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer

Manikandan Kadirvel, William T. Stimpson, Souad Moumene-Afifi, Biljana Arsic, Nicola Glynn, Nigel Halliday, Paul Williams, Peter Gilbert, Andrew J. McBain, Sally Freeman, John M. Gardiner^*

^*Corresponding author for this work

Chemical Engineering

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

14 Citations (Scopus)

Abstract

The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed 'quorum sensing', amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from d-mannitol via (2R)-2,3-O-isopropylideneglyceraldehyde. The synthesized enantiomers of DPD have AI-2 bioluminescence-inducing properties in the Vibrio harveyi BB170 strain.

Original language	English
Pages (from-to)	2625-2628
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	8
Early online date	19 Feb 2010
DOIs	https://doi.org/10.1016/j.bmcl.2010.02.064
Publication status	Published - 15 Apr 2010

Keywords

AI-2
Autoinducer
DPD

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Access to Document

10.1016/j.bmcl.2010.02.064Licence: None: All rights reserved

Cite this

Kadirvel, M., Stimpson, W. T., Moumene-Afifi, S., Arsic, B., Glynn, N., Halliday, N., Williams, P., Gilbert, P., McBain, A. J., Freeman, S., & Gardiner, J. M. (2010). Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer. Bioorganic and Medicinal Chemistry Letters, 20(8), 2625-2628. https://doi.org/10.1016/j.bmcl.2010.02.064

@article{1192a26804934797ae1e05c52e04cf7e,

title = "Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer",

abstract = "The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed 'quorum sensing', amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from d-mannitol via (2R)-2,3-O-isopropylideneglyceraldehyde. The synthesized enantiomers of DPD have AI-2 bioluminescence-inducing properties in the Vibrio harveyi BB170 strain.",

keywords = "AI-2, Autoinducer, DPD",

author = "Manikandan Kadirvel and Stimpson, {William T.} and Souad Moumene-Afifi and Biljana Arsic and Nicola Glynn and Nigel Halliday and Paul Williams and Peter Gilbert and McBain, {Andrew J.} and Sally Freeman and Gardiner, {John M.}",

year = "2010",

month = apr,

day = "15",

doi = "10.1016/j.bmcl.2010.02.064",

language = "English",

volume = "20",

pages = "2625--2628",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier",

number = "8",

}

Kadirvel, M, Stimpson, WT, Moumene-Afifi, S, Arsic, B, Glynn, N, Halliday, N, Williams, P, Gilbert, P, McBain, AJ, Freeman, S & Gardiner, JM 2010, 'Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer', Bioorganic and Medicinal Chemistry Letters, vol. 20, no. 8, pp. 2625-2628. https://doi.org/10.1016/j.bmcl.2010.02.064

TY - JOUR

T1 - Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer

AU - Kadirvel, Manikandan

AU - Stimpson, William T.

AU - Moumene-Afifi, Souad

AU - Arsic, Biljana

AU - Glynn, Nicola

AU - Halliday, Nigel

AU - Williams, Paul

AU - Gilbert, Peter

AU - McBain, Andrew J.

AU - Freeman, Sally

AU - Gardiner, John M.

PY - 2010/4/15

Y1 - 2010/4/15

N2 - The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed 'quorum sensing', amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from d-mannitol via (2R)-2,3-O-isopropylideneglyceraldehyde. The synthesized enantiomers of DPD have AI-2 bioluminescence-inducing properties in the Vibrio harveyi BB170 strain.

AB - The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed 'quorum sensing', amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from d-mannitol via (2R)-2,3-O-isopropylideneglyceraldehyde. The synthesized enantiomers of DPD have AI-2 bioluminescence-inducing properties in the Vibrio harveyi BB170 strain.

KW - AI-2

KW - Autoinducer

KW - DPD

UR - http://www.scopus.com/inward/record.url?scp=77950063417&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2010.02.064

DO - 10.1016/j.bmcl.2010.02.064

M3 - Article

C2 - 20307979

AN - SCOPUS:77950063417

SN - 0960-894X

VL - 20

SP - 2625

EP - 2628

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 8

ER -

Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this