137233-53-5Relevant articles and documents
Stereoselective synthesis of uridine-derived nucleosyl amino acids
Spork, Anatol P.,Wiegmann, Daniel,Granitzka, Markus,Stalke, Dietmar,Ducho, Christian
experimental part, p. 10083 - 10098 (2012/02/05)
Novel hybrid structures of 5′-deoxyuridine and glycine were conceived and synthesized. Such nucleosyl amino acids (NAAs) represent simplified analogues of the core structure of muraymycin nucleoside antibiotics, making them useful synthetic building blocks for structure-activity relationship (SAR) studies. The key step of the developed synthetic route was the efficient and highly diastereose-lective asymmetric hydrogenation of didehydro amino acid precursors toward protected NAAs. It was anticipated that the synthesis of unprotected muraymycin derivatives via this route would require a suitable intermediate protecting group at the N-3 of the uracil base. After initial attempts using PMB- and BOM-N-3 protection, both of which resulted in problematic deprotection steps, an N-3 protecting group-free route was envisaged. In spite of the pronounced acidity of the uracil-3-NH, this route worked equally efficient and with identical stereoselectivities as the initial strategies involving N-3 protection. The obtained NAA building blocks were employed for the synthesis of truncated 5′-deoxymuraymycin analogues (Figure presented).
Improved convergent synthesis of 5'-epi-analogues of muraymycin nucleoside antibiotics
Spork, Anatol P.,Koppermann, Stefan,Ducho, Christian
scheme or table, p. 2503 - 2507 (2010/01/16)
Nucleoside antibiotics represent a promising class of natural products for the development of novel antibacterial agents, with particular respect to structurally simplified analogues maintaining biological activity. There are established truncated 5-epi-d
Synthetic studies of the tunicamycin antibiotics. Preparation of (+)-tunicaminyluracil, (+)-tunicamycin-V, and 5′-epi-tunicamycin-V
Myers, Andrew G.,Gin, David Y.,Rogers, Daniel H.
, p. 4697 - 4718 (2007/10/02)
A concise synthetic route to the tunicamycin antibiotics is described, illustrated by the preparation of (+)-tunicamycin-V (1-V). Key features of the synthesis include (1) the development and application of a silicon-mediated reductive coupling of aldehydes and allylic alcohols to construct the undecose core of the natural product and (2) the development of an efficient procedure for the synthesis of the trehalose glycosidic bond within the antibiotic. These innovations allow for the coupling of a uridine-derived aldehyde fragment with a performed trehalose-linked disaccharide allylic alcohol to form the carbohydrate core (1) of the natural product in a highly covergent manner. The resultant amino polyol is a versatile intermediate for the synthesis of any of the homologous tunicamycin antibiotics.
