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Synthesis 1996; 1996(12): 1468-1472
DOI: 10.1055/s-1996-4417
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On the Synthesis of Naphthoquinonyl Heterocyclic Amino Acids

Prativa Bade Shrestha-Dawadi1 , Shmuel Bittner1 , Mati Fridkin2 , Shai Rahimipour2
  • 1Department of Chemistry, Ben Gurion University of the Negev, Beer Sheva 84105, Israel
  • 2The Weizman Institute of Science, Rehovot 76100, Israel
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Publication History

Publication Date:
31 December 2000 (online)

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L-Histidine, N α -cbz-L-histidine, L-tryptophan and L-proline react with 1,4-naphthoquinone or 2,3-dichloro-1,4-naphthoquinone to afford modified N-quinonyl amino acids. With free α-amino acids, the quinone moiety is attached to the α-amino group. With blocked α-amino acids the quinone moiety is attached to the heterocyclic nitrogen atom.

1,4-naphthoquinone - 2,3-dichloro-1,4-naphthoquinone - α-amino acids - N-quinonyl amino acids - Michael addition