高等学校化学学报

高等学校化学学报 ›› 2000, Vol. 21 ›› Issue (S1): 457.

• Synthetic Sciences • 上一篇    下一篇

Enantioselective Construction of the Oxidized Tryptophan Fragment of TMC-95A and TMC-95B

MA Da-Wei, WU Qing-Quan   

  1. State Key Laboratory of Bio-organic and Natural Product Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032
  • 出版日期:2000-12-31 发布日期:2000-12-31

Enantioselective Construction of the Oxidized Tryptophan Fragment of TMC-95A and TMC-95B

MA Da-Wei, WU Qing-Quan   

  1. State Key Laboratory of Bio-organic and Natural Product Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032
  • Online:2000-12-31 Published:2000-12-31

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被引次数

4

摘要：

TMC-95A-D are four cyclic peptides containing L-tyrosine, L-asparagine, highly oxidized L-tryptophan, (Z)-1-propenylmine and 3-methyl-2-oxo-pentanoic acid units. These compounds were recently isolated from the fermentation broth of Apiospora montagnei Sacc.TC 1093,isolated from a soil sample. Biological studies indicated that these natural products, especially TMC-95A, exhibit potent inhibiting activity towards proteasome (IC50=5.4 nM). In this report, a stereocontrolled synthesis of the oxidized tryptophan fragment of TMC-95A and TMC-95B is described. Key steps include the condensation of the lithiated oxindole with D-Gamer aldehyde and subsequent dihydroxylatioa of the carbon-carbon double bond.

Abstract:

TMC-95A-D are four cyclic peptides containing L-tyrosine, L-asparagine, highly oxidized L-tryptophan, (Z)-1-propenylmine and 3-methyl-2-oxo-pentanoic acid units. These compounds were recently isolated from the fermentation broth of Apiospora montagnei Sacc.TC 1093,isolated from a soil sample. Biological studies indicated that these natural products, especially TMC-95A, exhibit potent inhibiting activity towards proteasome (IC50=5.4 nM). In this report, a stereocontrolled synthesis of the oxidized tryptophan fragment of TMC-95A and TMC-95B is described. Key steps include the condensation of the lithiated oxindole with D-Gamer aldehyde and subsequent dihydroxylatioa of the carbon-carbon double bond.

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