A stereoselective synthesis of the urinary metabolite  N-acetyl-S-(3,4-dihydroxybutyl)cysteine

Sharma, Kamlesh; Laurens, Johannes B.; Pilcher, Lynne A.

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dc.contributor.author	Sharma, Kamlesh
dc.contributor.author	Laurens, Johannes B.
dc.contributor.author	Pilcher, Lynne A.
dc.date.accessioned	2017-02-28T11:29:20Z
dc.date.available	2017-02-28T11:29:20Z
dc.date.issued	2009
dc.description.abstract	On exposure to the potential carcinogen 1,3-butadiene, the major urinary metabolite in humans is N-acetyl-S-(3,4-dihydroxybutyl)cysteine. A novel, stereoselective synthesis of this cysteine–butadiene metabolite has been developed that is suitable for the production of either diastereomer for use in occupational exposure analysis. L-Cysteine and 4-bromo-1-butene are coupled via an SN2 reaction to give the core structure. A Sharpless asymmetric dihydroxylation using the dihydroquinidine (DHQD) ligand provided the terminal 1,2-diol with the 3-hydroxyl group in the R configuration. Supplementary materials are available for this article. Go to the publisher’s online edition of Synthetic Communications1 to view the free supplemental resource	en_ZA
dc.description.department	Chemistry	en_ZA
dc.description.librarian	hb2017	en_ZA
dc.description.sponsorship	The National Research Foundation of South Africa and the University of Pretoria.	en_ZA
dc.description.uri	http://www.tandfonline.com/loi/lsyc20	en_ZA
dc.identifier.citation	Kamlesh Sharma , J. B. Laurens & Lynne A. Pilcher (2009) Stereoselective Synthesis of the Urinary Metabolite N-Acetyl-S-(3,4-dihydroxybutyl)cysteine, Synthetic Communications, 39:8, 1415-1424, DOI: 10.1080/00397910802527763.	en_ZA
dc.identifier.issn	0039-7911 (print)
dc.identifier.issn	1532-2432 (online)
dc.identifier.other	10.1080/00397910802527763
dc.identifier.uri	http://hdl.handle.net/2263/59199
dc.language.iso	en	en_ZA
dc.publisher	Routledge	en_ZA
dc.rights	© Taylor & Francis Group, LLC. This is an electronic version of an article published in Synthetic Communications, vol. 39, no. 8, pp. 1415-1424, 2009. doi : 10.1080/00397910802527763. Synthetic Communications is available online at : http://www.tandfonline.comloi/lsyc20.	en_ZA
dc.subject	Dihydroxylation	en_ZA
dc.subject	Stereoselective synthesis	en_ZA
dc.subject	Urinary metabolite	en_ZA
dc.subject	N-acetyl-S-(3,4-dihydroxybutyl)cysteine	en_ZA
dc.subject	Cysteine–butadiene metabolite	en_ZA
dc.title	A stereoselective synthesis of the urinary metabolite N-acetyl-S-(3,4-dihydroxybutyl)cysteine	en_ZA
dc.type	Postprint Article	en_ZA