Total Synthesis and Stereochemistry Revision of Mannopeptimycin Aglycone

被引：1

作者：

Fuse, Shinichiro ^{[1
]}

Tanaka, Hiroshi ^{[2
]}

Takahashi, Takashi ^{[3
]}

Doi, Takayuki ^{[4
]}

机构：

[1] Tokyo Inst Technol, Inst Innovat Res, Midori Ku, R1-13,4259 Nagatsuta Cho, Yokohama, Kanagawa 2268503, Japan

[2] Tokyo Inst Technol, Sch Mat & Chem Technol, Meguro Ku, H-101,2-12-1 Ookayama, Tokyo 1528552, Japan

[3] Yokohama Univ Pharm, Dept Pharmaceut Sci, Totsuka Ku, 601 Matano Cho, Yokohama, Kanagawa 2450066, Japan

[4] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, 6-3 Aza Aoba, Sendai, Miyagi 9808578, Japan

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 2017年 / 75卷 / 12期

关键词：

mannopeptimycin; aglycone; antibiotic; glycopeptide; guanidine; unnatural amino acid; cyclic peptide; asymmetric aldol; macrolactamization; structural revision; GLYCOSYL ORTHO-ALKYNYLBENZOATES; GRAM-POSITIVE BACTERIA; UNUSUAL AMINO-ACIDS; GLYCOPEPTIDE ANTIBIOTICS; BETA-HYDROXYENDURACIDIDINES; STREPTOMYCES-HYGROSCOPICUS; DERIVATIVES; ANTIBACTERIAL; AGENTS; ALPHA;

D O I：

10.5059/yukigoseikyokaishi.75.1274

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mannopeptimycin is an attractive drug candidate due to its strong antimicrobial activity against drug-resistant strains. However, detailed elucidation of structure-activity relationship and its mode of action has been hampered because the chemical synthesis of the densely functionalized aglycone moiety consisting of cyclic hexapeptide was not established. The key point in the synthesis of the aglycone was the construction of densely functionalized unnatural amino acids, Aiha-A and Aiha-B. This account describes isolation, structural determination of mannopeptimycins, previously reported synthesis of Aiha-A and Aiha-B as well as our short-step, high yielding synthesis of Aihas leading to the first synthesis of mannopeptimycin aglycone with stereo chemistry revision of originally proposed structure.

引用

页码：1274 / 1285

页数：12

共 35 条

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De Voe S. E., 1970, U. S. Patent, Patent No. 3495004

[2] ASYMMETRIC-SYNTHESIS OF UNUSUAL AMINO-ACIDS - AN EFFICIENT SYNTHESIS OF OPTICALLY PURE ISOMERS OF BETA-METHYLPHENYLALANINE [J].