ISSN:
0170-2041
Keywords:
L-Proline, S-alkyl-5-thioxo-, N-acyl-5-thioxo-
;
Peptide building blocks
;
5-Thioxo-L-proline
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
We herein report an improved synthetic pathway to 5-thioxo-L-proline (2) (using R,S nomenclature, the L form here possesses the S configuration). Compound 2 is synthesized from naturally occurring 5-oxo-L-proline (1) at room temperature with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (3) (Lawesson′s reagent, LR). The synthesis is an improved version of our previously published method. The optical purity of 2 has been proven by thin-layer chromatography based on chiral ligand exchange. The synthesis of N-acyl and S-alkyl derivatives of 5-thioxo-L-proline (Top-OH), 5-thioxo-L-proline methyl ester (Top-OCH3), and the pseudodipeptide Boc-L-Phe-Top-OCH3 is also described.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198919890231
Permalink