81081-42-7Relevant academic research and scientific papers
Conversion of "customizable Units" into N-Alkyl Amino Acids and Generation of N-Alkyl Peptides
Saavedra, Carlos J.,Carro, Carmen,Hernández, Dácil,Boto, Alicia
supporting information, p. 8392 - 8410 (2019/07/08)
An efficient conversion of hydroxyproline "customizable" units into new amino acids with a variety of N-alkyl substituents is described. The process is versatile and can afford valuable N-methyl amino acids and N,O-acetals. In addition, it allows the introduction of N-homoallylic substituents and N-chains with terminal ester, ketone, or cyano groups. These chains could be used for peptide extension or conjugation to other molecules (e.g., by olefin metathesis, peptide ligation, etc.). The transformation is carried out in just two (for R = CH2OAc) or three steps (scission of the pyrrolidine ring, manipulation of the α-chain, and the N-substituent) under mild, metal-free conditions, affording products with high optical purity.
Total synthesis and structure-activity relationships of caspofungin-like macrocyclic antifungal lipopeptides
Yao, Jianzhong,Liu, Hongming,Zhou, Ting,Chen, Hai,Miao, Zhenyuan,Dong, Guoqiang,Wang, Shengzheng,Sheng, Chunquan,Zhang, Wannian
supporting information; experimental part, p. 3074 - 3085 (2012/06/01)
The echinocandins represent a well-known class of macrocyclic antifungal lipopeptides that can be used for treatment of invasive fungal infections. Due to their complex chemical structures and synthetic difficulties, the structure-activity relationships (SARs) of them are still limited. A total synthetic approach was developed to synthesize structurally diverse caspofungin-like antifungal cyclic lipopeptides, allowing for systemically investigating their SARs. Most of the designed cyclic lipopeptides showed potent antifungal activities with broad spectrum. In particular, several compounds (e.g., 30a, 30e-h, 31a-d, 32c, and 33a,b) were more active in vitro against Candida albicans or Aspergillus fumigatus than caspofungin. The findings in this work indicated that the 'left' tripeptide segment of cyclic lipopeptide scaffold might be suitable for a hydrophilic structural motif, whereas the 'right' lipotripeptide segment was preferred as a hydrophobic core. The alkoxy-naphthoyl was found to be optimal side chain and alkyl length could affect the SARs of alkoxy-aroyl side chains.
