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