N2-(Γ-D-GLUTAMYL)-MESO-2-(L),2′(D)-DIAMINOPIMELIC ACID AS THE MINIMAL PREREQUISITE STRUCTURE OF FK-156: ITS ACYL DERIVATIVES WITH POTENT IMMUNOSTIMULATING ACTIVITY
N2-(Γ-D-GLUTAMYL)-MESO-2-(L),2′(D)-DIAMINOPIMELIC ACID AS THE MINIMAL PREREQUISITE STRUCTURE OF FK-156: ITS ACYL DERIVATIVES WITH POTENT IMMUNOSTIMULATING ACTIVITY
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N2-(γ-D-谷氨酰)-meso-2-(L),2′(D)-二氨基庚二酸作为 FK-156 的最小先决条件：其酰基衍生物具有有效的免疫刺激活性
DOI：
10.1002/chin.198240116
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发表时间：
1982
期刊：
影响因子：
--
通讯作者：
M. Hashimoto
中科院分区：
文献类型：
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作者：
Y. Kitaura;O. Nakaguchi;H. Takeno;S. Okada;S. Yonishi;K. Hemmi;J. Mori;H. Senoh;Y. Mine;M. Hashimoto
3， R= h4， R= CH3 (CH2) 6co5， R= CH3 (CH2) 16CO微生物代谢物，结构上与细菌细胞壁肽聚糖肽相似。与众所周知的muramyl二肽（MDP, 2）相比，1的结构是独特的，因为1在d -乳酸基侧链的0端没有氨基葡萄糖残基，而是在1的1 >谷氨酸的7-C端携带zneso- 2,2 '-二氨基基甘氨酸残基。特别令人感兴趣的是其广泛的免疫活性，尽管缺乏直到最近才被认为是生物活性所必需的muramyl部分。因此，我们认为1中的2,2′-二氨基戊酸可能与2中的muramyl部分一样，是其独特免疫活性的主要贡献者。作为该天然产物计划的一部分，我们对制备(1)(a)分离感兴趣：T. Gotoh， Y. Kuroda， M. Okumura， T. Tanaka， T. Nishiura， M. Kohsaka， H. Aoki和H. Imanaka，抗菌药物和化疗跨科学会议，21，芝加哥，IL, p 414, 1981，摘要。(b)合成：K. Hemmi， H. Takeno， S. Okada， O. Nakaguchi， Y. Kitaura， M.。
3, R= H 4, R= CH3 (CH2) 6CO 5, R= CH3 (CH2) 16CO microbial metabolite with a structurally close resemblance to thebacterial cell-wall peptidoglycan peptides. 1 The structure of 1 is unique, as compared with the well-known muramyl dipeptide (MDP, 2), in the respect that 1 is de-void of the glucosamine residue at the 0 terminal of the D-lactoyl side chain and instead carries the zneso-2, 2'-di-aminopimelylglycine residue at the 7-C terminal of the l> glutamic acid in 1. Of particular interest is its widerange of immunological activities despite the lack of the muramyl moiety which had, until recently, been considered to be essential for the biological activity. 2, 3 Therefore, it was considered that the 2, 2'-diaminopimeIic acid in 1, like the muramyl moiety in 2, might be a major contributor to the unique immunoactivity. As part of a program on this natural product, we were interested in preparing the (1)(a) Isolation: T. Gotoh, Y. Kuroda, M. Okumura, T. Tanaka, T. Nishiura, M. Kohsaka, H. Aoki, and H. Imanaka, Intersci-ence Conference on Antimicrobial Agents and Chemotherapy, 21st, Chicago, IL, p 414, 1981, abstr.(b) Synthesis: K. Hemmi, H. Takeno, S. Okada, O. Nakaguchi, Y. Kitaura, and M.