214467-60-4Relevant articles and documents
Synthesis and antibacterial activities of N-Glycosylated derivatives of tyrocidine a, a macrocyclic peptide antibiotic
Honggang, Hu,Jie, Xue,Swarts, Benjamin M.,Qianli, Wang,Qiuye, Wu,Zhongwu, Guo
experimental part, p. 2052 - 2059 (2009/12/30)
An efficient and practical method for macrocyclic glycopeptide synthesis was developed and utilized to synthesize tyrocidine A and its glycosylated derivatives. The method is based on solid-phase peptide synthesis using 2-chlorotrityl resin as the solid-phase support and glycosyl amino acids as building blocks. After glycopeptides with fully protected glycans and side chains were released from the acid-labile resin, their Cand N-termini were intramolecularly coupled in solution to afford cyclic glycopeptides in quantitative yields. This synthetic method should be generally applicable to various macrocyclic glycopeptides. Biological studies of the synthetic tyrocidine A derivatives showed that linking glycans directly to the Asn residue of tyrocidine A diminished its antibacterial activity, but linking glycans to Asn via a simple spacer did not. These results Revealed the important impact of glycans on the activities, and probably the structures, of glycopeptide antibiotics.
Synthesis and conformational analysis of pseudosugar analogues of chitotriose
Thiele, Gabriela,Rottmann, Antje,Germer, Antje,Kleinpeter, Erich,Spindler, Klaus-Dieter,Synstad, Bjornar,Eijsink, Vincent G. H.,Peter, Martin G.
, p. 471 - 489 (2007/10/03)
EDC mediated coupling of the 4-O-succinoyl glycosyl azide 2 with glycosylamine 3 gave the protected glycosylazide 4. Hydrogenation of 4 afforded the glycosylamine 5. Chemoselective hydrolysis of the reducing end glycosylamine, followed by hydrogenation af
