Synthesis of phakellistatin 13 and oxidation to phakellistatin 3 and isophakellistatin 3.
Synthesis of phakellistatin 13 and oxidation to phakellistatin 3 and isophakellistatin 3.
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DOI：
10.1002/chin.200440187
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发表时间：
2004-04
期刊：
影响因子：
5.2
通讯作者：
Kevin Greenman;Dana M. Hach;D. L. Van Vranken
中科院分区：
文献类型：
--
作者：
Kevin Greenman;Dana M. Hach;D. L. Van Vranken
The natural product phakellistatin 13 cyclo-(TrpProPheGlyProThrLeu) was synthesized. Photosensitized oxidation of phakellistatin 13 gave the natural products phakellistatin 3 and isophakellistatin 3, demonstrating for the first time that a tryptophan residue can be directly converted to the corresponding 3a-hydroxypyrrolo[2,3-b]indoline in a full length peptide. Competitive oxidation of the indoline product was identified as the cause of low mass balance and is probably the source of low mass balance in the oxidative cyclization of all tryptamine derivatives. [reaction--see text]
