1079926-41-2Relevant articles and documents
Suzuki-Miyaura Diversification of Amino Acids and Dipeptides in Aqueous Media
Willemse, Tom,Van Imp, Karolien,Goss, Rebecca J. M.,Van Vlijmen, Herman W. T.,Schepens, Wim,Maes, Bert U. W.,Ballet, Steven
, p. 2055 - 2070 (2015)
The Suzuki-Miyaura derivatisation of free amino acids, peptides and proteins is an attractive area with considerable potential utility for medicinal chemistry and chemical biology. Here we report the modification of unprotected and Boc-protected aromatic amino acids and dipeptides in aqueous media, enabling heteroarylation and vinylation. We systematically investigate the impact of the peptide backbone and adjacent amino acid residues upon the reaction. Our studies reveal that although asparagine and histidine hinder the reaction, by utilising dppf, a ferrocene-based bidentate phosphine ligand, cross coupling of halophenylalanine or halotryptophan adjacent to such a residue could be enabled. Our studies reveal dppf to have good compatibility with all unprotected, proteinogenic amino acid side chains.
Gene expression enabling synthetic diversification of natural products: Chemogenetic generation of pacidamycin analogs
Roy, Abhijeet Deb,Grueschow, Sabine,Cairns, Nickiwe,Goss, Rebecca J. M.
supporting information; experimental part, p. 12243 - 12245 (2010/11/19)
Introduction of prnA, the halogenase gene from pyrrolnitrin biosynthesis, into Streptomyces coeruleorubidus resulted in efficient in situ chlorination of the uridyl peptide antibotic pacidamycin. The installed chlorine provided a selectably functionalizable handle enabling synthetic modification of the natural product using mild cross-coupling conditions in crude aqueous extracts of the culture broth.
