Herein we describe a convenient method for the synthesis of the β-substituted Cys analogs 1a, b and trans-β-mercapto proline 1c, from their corresponding α,β-unsaturated-α-amino esters using p-methoxybenzyl mercaptan as the sulfur source. The intermediate β-thioethers are stable toward chromatographic purification, and after global deprotection the β-mercapto amino acids 1a–c are obtained in good to high yields (64%–99%).

Convenient access to β-substituted cysteines and β- and γ-mercapto prolines / J.C. Hansen, M. Rabuffetti, L. Bunch. - In: CANADIAN JOURNAL OF CHEMISTRY. - ISSN 0008-4042. - 101:(2023), pp. 326-333. [10.1139/cjc-2022-0161]

Convenient access to β-substituted cysteines and β- and γ-mercapto prolines

M. Rabuffetti
Secondo
;
2023

Abstract

Herein we describe a convenient method for the synthesis of the β-substituted Cys analogs 1a, b and trans-β-mercapto proline 1c, from their corresponding α,β-unsaturated-α-amino esters using p-methoxybenzyl mercaptan as the sulfur source. The intermediate β-thioethers are stable toward chromatographic purification, and after global deprotection the β-mercapto amino acids 1a–c are obtained in good to high yields (64%–99%).
cysteine analogs; proline analogs
Settore CHIM/06 - Chimica Organica
2023
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/957542
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? 0
social impact