An efficient method for the synthesis of long-chain α,ω-diamino acids, starting from natural α-amino acids, has been developed. The long-chain skeleton has been generated through condensation between a protected aldehyde, derived from l-aspartic acid, and an ylide obtained from an ω-hydroxy-alkyl phosphonium salt. After conversion of the ω-hydroxy group into an amine, catalytic hydrogenation produced the N, N′-protected α,ω-diamino acid. The present route to α,ω-diamino acids allows the modulation of the chain length depending on the length of the ylide used for the Wittig olefination reaction.

A practical route to long-chain non-natural α,ω-diamino acids / G. Brasile, L. Mauri, S. Sonnino, F. Compostella, F. Ronchetti. - In: AMINO ACIDS. - ISSN 0939-4451. - 44:2(2013 Feb), pp. 435-441. [10.1007/s00726-012-1349-0]

A practical route to long-chain non-natural α,ω-diamino acids

G. Brasile
Primo
;
L. Mauri
Secondo
;
S. Sonnino;F. Compostella
;
F. Ronchetti
Ultimo
2013

Abstract

An efficient method for the synthesis of long-chain α,ω-diamino acids, starting from natural α-amino acids, has been developed. The long-chain skeleton has been generated through condensation between a protected aldehyde, derived from l-aspartic acid, and an ylide obtained from an ω-hydroxy-alkyl phosphonium salt. After conversion of the ω-hydroxy group into an amine, catalytic hydrogenation produced the N, N′-protected α,ω-diamino acid. The present route to α,ω-diamino acids allows the modulation of the chain length depending on the length of the ylide used for the Wittig olefination reaction.
α,ω-Diamino acids ; Lipidic α-amino acids (LAAs) ; Unnatural fatty acids ; Wittig olefination
Settore BIO/10 - Biochimica
feb-2013
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/208944
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