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Synthesis of (S)-5,6-dibromo-tryptophan derivatives as building blocks for peptide chemistry

✍ Scribed by Adriano Mollica; Azzurra Stefanucci; Federica Feliciani; Gino Lucente; Francesco Pinnen

Book ID
104099054
Publisher
Elsevier Science
Year
2011
Tongue
French
Weight
205 KB
Volume
52
Category
Article
ISSN
0040-4039

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✦ Synopsis

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-dibromotryptophan derivatives is reported. The reaction is performed by using 6-Br-isatin as starting material.

Selective bromination at position 5 was followed by BH 3 reduction of the intermediate a-keto-amide and alkylation with Ser-OH in Ac 2 O/AcOH. Optical resolution was effected by enzymatic de-acetylation of the obtained racemic mixture. Finally, in situ N a -Boc protection of the optically pure S form yielded the desired N a -Boc-(S)-5,6-dibromo-tryptophan.

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