90048-49-0Relevant articles and documents
Optimized syntheses of Fmoc azido amino acids for the preparation of azidopeptides
Pícha, Jan,Budě?ínsky, Milo?,Machá?ková, Kate?ina,Collinsová, Michaela,Jirá?ek, Ji?í
, p. 202 - 214 (2017/04/06)
The rise of CuI-catalyzed click chemistry has initiated an increased demand for azido and alkyne derivatives of amino acid as precursors for the synthesis of clicked peptides. However, the use of azido and alkyne amino acids in peptide chemistry is complicated by their high cost. For this reason, we investigated the possibility of the in-house preparation of a set of five Fmoc azido amino acids: β-azido l-alanine and d-alanine, γ-azido l-homoalanine, δ-azido l-ornithine and ω-azido l-lysine. We investigated several reaction pathways described in the literature, suggested several improvements and proposed several alternative routes for the synthesis of these compounds in high purity. Here, we demonstrate that multigram quantities of these Fmoc azido amino acids can be prepared within a week or two and at user-friendly costs. We also incorporated these azido amino acids into several model tripeptides, and we observed the formation of a new elimination product of the azido moiety upon conditions of prolonged couplings with 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate/DIPEA. We hope that our detailed synthetic protocols will inspire some peptide chemists to prepare these Fmoc azido acids in their laboratories and will assist them in avoiding the too extensive costs of azidopeptide syntheses. Experimental procedures and/or analytical data for compounds 3–5, 20, 25, 26, 30 and 43–47 are provided in the supporting information.
Towards new MraY inhibitors: A serine template for uracil and 5-amino-5-deoxyribosyl scaffolding
Le Corre, Laurent,Gravier-Pelletier, Christine,Le Merrer, Yves
, p. 5386 - 5394 (2008/03/18)
The bacterial translocase MraY is a good target for the development of new antitbiotics as it is ubiquitous and essential for bacterial growth. The goal of this work was the synthesis of simplified analogues of naturally occurring inhibitors of this enzyme to investigate the essential character of the uridine moiety of these inhibitors with regards to biological activity. Thus, the structure of the targeted enantiomerically pure N-(uracilylpentyl)-β-D-O- (5-amino-5-deoxyribosyl)-L-serine retains uracil and 5-amino-5-deoxyribose parts linked by a serinyl template. The synthetic strategy towards this compound relies on sequential O-glycosylation and N-alkylation by reductive amination of a serine derivative. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
CIDOFOVIR PEPTIDE CONJUGATES AS PRODRUGS
-
Page/Page column 13-14, (2008/06/13)
Cidofovir-based compounds having an amino acid, dipeptide or tripeptide attached to a cidofovir or cyclic cidofovir framework. The compounds show enhanced oral bioavailability and increased binding to the PepT1 transporter. The present invention also provides compositions and methods for treating virus infections, and a method of preparing cidofovir.
