新产品编号:487765
Chemical Name: 3(S)-[5(S)-[2(S)-Amino-4-pentenamido]-2(S),3(R),4(R),6-tetrahydroxyhexanamido]-3-phenylpropionic acid hydrochloride
CAS No. 219813-22-6 (free base)
项目整合开发状态: Biological Testing
项目研究机构: Takeda (Originator)
合成路线:Pyloricidin C (I) is isolated from the fermentation broth of Bacillus sp.HC-70.Enzymatic hydrolysis of the N-terminal leucyl moiety of (I) by the action of actinase E leads to dipeptide (II).N-Boc-(S)-2-amino-4-pentenoic acid (III) is activated as the corresponding succinimidyl ester (IV) upon treatment with N hydroxysuccinimide and DCC.Then,coupling of dipeptide (II) with the active ester (IV) furnishes the tripeptide derivative (V).Finally,the N-Boc protecting group of (V) is removed by treatment with HCl in EtOAc to yield the title compound.
📌 参考资料/链接：
参考文献标题:Polyol-amino acid cpds.having anti-Helicobacter pylori activity
文献作者:Akiyama,Y.; Nakano,Y.; Tsubotani,S.; Izawa,M.; Nakao,M.; Miyagawa,K.; Kamiyama,K.; Nishikimi,Y.(Takeda Chemical Industries,Ltd.)
参考来源:EP 0998488; JP 1999080109; WO 9902549
📄 详细内容
合成路线:Pyloricidin C (I) is isolated from the fermentation broth of Bacillus sp.HC-70.Enzymatic hydrolysis of the N-terminal leucyl moiety of (I) by the action of actinase E leads to dipeptide (II).N-Boc-(S)-2-amino-4-pentenoic acid (III) is activated as the corresponding succinimidyl ester (IV) upon treatment with N hydroxysuccinimide and DCC.Then,coupling of dipeptide (II) with the active ester (IV) furnishes the tripeptide derivative (V).Finally,the N-Boc protecting group of (V) is removed by treatment with HCl in EtOAc to yield the title compound.
参考文献标题:Synthesis and anti-Helicobacter pylori activity of pyloricidin derivatives.I.Structure-activity relationships on the terminal peptidic moiety
文献作者:Hasuoka,A.; Nishikimi,Y.; Nakayama,Y.; Kamiyama,K.; Nakao,M.; Miyagawa,K-I.; Nishimura,O.; Fujino,M.
参考来源:J Antibiot 2002,55(3),322