Synthesis of N-Fmoc-α-amino acids carrying the four DNA nucleobases in the side chain.

✍ Scribed by Paola Ciapetti; Francesco Soccolini; Maurizio Taddei

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 766 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)01047-2

✦ Synopsis

Four new N-Fmoc cc-amino acids carrying a nucleobase in the side chain were prepared starting from L-glutamic acid. N-Boc-glutamic acid ct benzyl ester underwent a radical decarboxylation in the presence of CBrCl3 to give the corresponding 2-amino-4-bromobutanoic acid derivative. The four nucleobases (adenine, cytosine, thymine and guanine) were introduced "via" nucleophilic substitution of the bromide using a different synthetic protocol for each base.The Boc protection was changed to Fmoc and the benzyl ester deprotected to give the four amino acids in good yields and in a suitable form for solid phase peptide synthesis. The preparation of the insecticidal dipeptide NK 374200 is also described.