Transformation of alfa-Hydroxymethylamino Acids into alfa--Mercaptomethylamino Acids (alfa-Alkylcysteines)*[1]

• Autorzy: Olma A.
• Języki publikacji: EN

Abstrakty

EN

N-Boc-_-alkylserines (_-hydroxymethylamino acids) undergo a cyclization reaction without racemization to N-Boc-_-alkylserine-_-lactones in 90-98% yield using Mitsunobu conditions (Ph P, diethyl azodicarboxylate). Treatment of the corresponding _-lactones with sulphur nucleophiles (thiolacetic acid or 4-methoxybenzylmercaptan) gives S-protected N-Boc-_-alkylcysteines (_-mercaptomethylamino acids) in high yield. These chimeric _,_-disubstituted amino acids, being incorporated into peptide chain, are able to close the cyclic structure as a disulfide bond.

Słowa kluczowe

EN

alfa-mercaptomethylamino acids; alfa-hydroxymethylamino acids; alfa; alfa-disubstituted amino acids; Mitsunobu reaction

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2004
• Tom: Vol. 78 / nr 6
• Strony: 831--835

Twórcy

autor

Olma A.

• Institute of Organic Chemistry, Technical University, 90-924 Łódź, Żeromskiego 116, Poland,

Bibliografia

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