Total synthesis of an antifungal cyclic depsipeptide aureobasidin A

被引：32

作者：

Kurome, T

Inami, K

Inoue, T

Ikai, K

Takesako, K

Kato, I

Shiba, T

机构：

[1] TAKARA SHUZO CO LTD,BIOTECHNOL RES LABS,OTSU,SHIGA 52021,JAPAN

[2] PROT RES FDN,PEPTIDE INST,OSAKA 562,JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 12期

关键词：

D O I：

10.1016/0040-4020(96)00132-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of antifungal cyclic depsipeptide aureobasidin A is described. The synthesis was achieved mainly using bromotris(pyrrolidino)phosphonium hexafluorophosphate (PyBroP) as a coupling reagent. Peptide cyclization was carried out between L-allo-isoleucine (L-alle(1)) and L-Pro(9) residues in the linear nonapeptide at the final step of the synthesis. Synthesized aureobasidin A was completely identical with the natural antibiotic with respect to antifungal activity and physicochemical properties. Unusual reactions due to N-methylamino acid, an oxazoline-mediated reaction and an N, O-acyl migration, are also described.

引用

页码：4327 / 4346

页数：20

共 20 条

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