Stereoselective α-Deuteration of Serine, Cysteine, Selenocysteine, and 2,3-Diaminopropanoic Acid Derivatives

Autor:	Navo, Claudio D., Oroz, Paula, Mazo, Nuria, Blanco, Marina, Peregrina, Jesús M., Jiménez-Osés, Gonzalo, 0000-0003-0161-412X, 0000-0001-6049-0871, 0000-0003-3778-7065, 0000-0003-0105-4337
Rok vydání:	2022
Předmět:	Alcohols Carbocysteine Organic Chemistry Serine beta-Alanine Cysteine Amines Physical and Theoretical Chemistry Biochemistry Selenocysteine
Zdroj:	Organic Letters. 24:6810-6815
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.2c02715
Popis:	Efficient methodologies for synthesizing enantiopure α-deuterated derivatives of serine, cysteine, selenocysteine, and 2,3-diaminopropanoic acid have been developed. H/D exchange was achieved by deprotonation of a chiral bicyclic serine equivalent followed by selective deuteration. Additionally, diastereoselective additions of thiols, selenols, and amines to a chiral bicyclic dehydroalanine in deuterated alcohols allowed site-selective deuteration at the Cα atom of cysteine, selenocysteine, and 2,3-diaminopropanoic acid derivatives. A deuterated analogue of carbocysteine, a drug for the treatment of bronchiectasis, was synthesized.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e6a2c9fc249769554255d4a56b3451d4 https://doi.org/10.1021/acs.orglett.2c02715 Zobrazit plný text záznamu