Synthesis of (S)-5,6-dibromo-tryptophan derivatives as building blocks for peptide chemistry |
| |
Authors: | Adriano Mollica Azzurra StefanucciFederica Feliciani Gino LucenteFrancesco Pinnen |
| |
Institution: | a Dipartimento di Scienze del Farmaco, Università di Chieti-Pescara ‘G. d’Annunzio’, Via dei Vestini 31, 66100 Chieti, Italy b Istituto di Chimica Biomolecolare (CNR) c/o Dipartimento di Chimica e Tecnologie del Farmaco, ‘Sapienza’, Università di Roma, P.le A. Moro, 00185 Roma, Italy |
| |
Abstract: | 5,6-Dibromo-tryptophan is an interesting amino acid whose derivatives and analogues are found in a variety of highly bioactive natural compounds. Notwithstanding its relevance no data concerning this compound are found in the literature. Here an efficient pathway for the synthesis of 5,6-dibromo-tryptophan derivatives is reported. The reaction is performed by using 6-Br-isatin as starting material. Selective bromination at position 5 was followed by BH3 reduction of the intermediate α-keto-amide and alkylation with Ser-OH in Ac2O/AcOH. Optical resolution was effected by enzymatic de-acetylation of the obtained racemic mixture. Finally, in situ Nα-Boc protection of the optically pure S form yielded the desired Nα-Boc-(S)-5,6-dibromo-tryptophan. |
| |
Keywords: | Brominated amino acids Indole Isatin Racemic resolution Tryptophan |
本文献已被 ScienceDirect 等数据库收录! |
|