A practical route to long-chain non-natural alpha,omega-diamino acids

作者：Brasile Giuseppina; Mauri Laura; Sonnino Sandro; Compostella Federica^*; Ronchetti Fiamma

来源：Amino Acids, 2013, 44(2): 435-441.

DOI：10.1007/s00726-012-1349-0

• Lipidic alpha-amino acids (LAAs)
• Unnatural fatty acids
• Wittig olefination
• alpha,omega-Diamino acids

An efficient method for the synthesis of long-chain alpha,omega-diamino acids, starting from natural alpha-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 omega-hydroxy-alkyl phosphonium salt. After conversion of the omega-hydroxy group into an amine, catalytic hydrogenation produced the N,N%26apos;-protected alpha,omega-diamino acid. The present route to alpha,omega-diamino acids allows the modulation of the chain length depending on the length of the ylide used for the Wittig olefination reaction.

• 出版日期2013-2