188774-99-4Relevant academic research and scientific papers
A silver-promoted solid-phase guanidylation process enables the first total synthesis of stictamide A
Li, Xiang,Li, Yu-Lei,Chen, Yan,Zou, Yan,Zhuo, Xiao-Bin,Wu, Qiu-Ye,Zhao, Qing-Jie,Hu, Hong-Gang
, p. 94654 - 94657 (2015/11/24)
The first total synthesis of stictamide A, a structurally unique peptide with a statine motif and a N-prenyl modified arginine in the side chain, is disclosed. The requisite statine was achieved via stereoselective hydrogenation of a functionalized ketone. The N-prenyl modified arginine was constructed by a novel silver-promoted solid-phase strategy for the first time. This synthetic method can be generally applied to the efficient synthesis of peptides containing statine and/or arginine N-alkylation groups.
Total synthesis and stereochemical reassignment of tasiamide B
Sun, Tiantian,Zhang, Wei,Zong, Chengli,Wang, Peng,Li, Yingxi
, p. 364 - 374 (2011/03/22)
The first total synthesis of tasiamide B, an octapeptide bearing 4-amino-3-hydroxy-5-phenylpentanoic acid unit isolated from the marine cyanobacteria Symploca sp. is described. A simple and efficient way was found to avoid the pyroglutamylation of Nα-Me-Gln and led to a reassignment of the Nα-Me-L-Phe of tasiamide B to be N α-Me-D-Phe, which was also supported by 1D and 2D NMR. Copyright
An efficient synthesis of γ-amino β-ketoester by cross-Claisen condensation with α-amino acid derivatives
Honda, Yutaka,Katayama, Satoshi,Kojima, Mitsuhiko,Suzuki, Takayuki,Izawa, Kunisuke
, p. 3163 - 3166 (2007/10/03)
Cross-ester condensation between N-protected amino acid ester and the lithium enolate prepared from alkyl acetate gave the corresponding β-ketoester in high yield without the formation of the tertiary alcohol that is commonly seen as by-product. This inte
Process for producing 3-amino-2-oxo-1-halogenopropane derivatives
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, (2008/06/13)
Compounds formed by reacting a protected amino acid with an alkali metal enolate of an alkyl acetate are reacted with a halogenating agent for halogenation of the 2-position, or a protected amino acid is reacted with an alkali metal enolate of an alkyl halogenoacetate, to form a 4-amino-3-oxo-2-halogenobutanoic acid ester derivative, and hydrolysis and decarboxylation are conducted to produce a 3-amino-2-oxo-1-halogenopropane derivative or its salt. The present method is a useful process for producing a 3-amino-2-oxo-1-halogenopropane derivatives which can easily be converted to a 3-amino-1,2-epoxypropane.
