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Three approaches to the synthesis of L-leucine selectively labelled with carbon-13 or deuterium in either diastereotopic methyl group

Title data

Fletcher, Matthew D. ; Harding, John R. ; Hughes, Rachael A. ; Kelly, Nicholas M. ; Schmalz, Holger ; Sutherland, Andrew ; Willis, Christine l.:
Three approaches to the synthesis of L-leucine selectively labelled with carbon-13 or deuterium in either diastereotopic methyl group.
In: Journal of the Chemical Society, Perkin Transactions 1. (2000) Issue 1 . - pp. 43-51.
ISSN 1364-5463
DOI: https://doi.org/10.1039/A907598D

Abstract in another language

Three approaches to the synthesis of L-leucine selectively labelled with carbon-13 or deuterium in either diastereotopic methyl group as well as at C-3 and C-4 are described. In all three methods the stereogenic centre at C-2 was created with total stereocontrol via a one-pot, two-enzyme catalysed procedure involving hydrolysis and reductive amination of a 2-keto ester. However, the approaches vary in the synthesis of the isotopically labelled 2-keto esters and in the production of the stereogenic centre at C-4 which was achieved either via alkylation of a propionylated Evans’ auxiliary with labelled iodomethane or by the diastereoselective conjugate addition of a labelled organocopper reagent to crotonate tethered to a chiral sultam. The latter approach proved most efficient and using the (1R,2S,3R)-3-[N-phenylsulfonyl-N-(3,5-dimethyldiphenyl)aminobornan-2-ol ester 27, [5-13C]-L-leucine was prepared with >98% de at C-4 and in 49% overall yield from the first labelled intermediate 28.

Further data

Item Type: Article in a journal
Refereed: Yes
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Macromolecular Chemistry II
Result of work at the UBT: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 12 Dec 2019 10:11
Last Modified: 12 Dec 2019 10:11
URI: https://eref.uni-bayreuth.de/id/eprint/53570