ISSN:
0947-3440
Keywords:
Vinylglycine
;
Photoelimination
;
Norrish-II photoreaction
;
Dipeptide
;
Peptide modification, photochemical
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Enantiomerically pure vinylglycine (4b) can be prepared from natural („chiral pool“) amino acids by photoelimination of γ-functionalized N-phthaloyl amino acid esters. Two routes have been developed: (a) a three-step synthesis of substrate 3b [PhtN-Met(SO)OMe] from (S)-methionine and subsequent photolysis, (b) the use of N-phthaloyl activated methyl 2-amino-4-chloro- or -4-bromobutanoates 3d, e which are available from (S)-methionine (four-step synthesis) or from (S)-homoserine (two-step synthesis). The photoelimination (of HOSMe from 3b and of HX from 3d, e) proceeds quantitatively and leads to N,C-protected vinylglycine 4a in high yields. This strategy could also be applied to peptide-bound substrates as was shown for the protected Met-Gly (5b) which was transformed into the N-protected vinylglycine-glycine dipeptide 6 in three steps.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199511275
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