1607433-86-2Relevant academic research and scientific papers
Synthesis of the Highly Branched Hexasaccharide Core of Chlorella Virus N-Linked Glycans
Lin, Sicheng,Lowary, Todd L.
, p. 16992 - 16996 (2018)
Chlorella viruses produce N-linked glycoproteins with carbohydrate moieties that differ in structure from all other N-linked glycans. In addition, unlike most viruses, these organisms do not hijack the biosynthetic machinery of the host to make glycocoproteins; instead, they produce their own carbohydrate-processing enzymes. A better understanding of the function and assembly of these fascinating and structurally-unprecedented glycans requires access to probe molecules. This work describes the first synthesis of a chlorella virus N-linked glycan, a highly branched hexasaccharide that contains the pentasaccharide present in all of the >15 structures reported to date. The target molecule includes a glucosyl-asparagine linkage and a “hyperbranched” fucose residue in which all of the hydroxyl groups are glycosylated. Both convergent and linear approaches were investigated with the latter being successful in providing the target in 16 steps and 13 % overall yield.
Expedient Route to Access Rare Deoxy Amino l-Sugar Building Blocks for the Assembly of Bacterial Glycoconjugates
Sanapala, Someswara Rao,Kulkarni, Suvarn S.
supporting information, p. 4938 - 4947 (2016/05/10)
Bacterial glycoproteins and oligosaccharides contain several rare deoxy amino l-sugars which are virtually absent in the human cells. This structural difference between the bacterial and host cell surface glycans can be exploited for the development of carbohydrate based vaccines and target specific drugs. However, the unusual deoxy amino l-sugars present in the bacterial glycoconjugates are not available from natural sources. Thus, procurement of orthogonally protected rare l-sugar building blocks through efficient chemical synthesis is a crucial step toward the synthesis of structurally well-defined and homogeneous complex glycans. Herein, we report a general and expedient methodology to access a variety of unusual deoxy amino l-sugars starting from readily available l-rhamnose and l-fucose via highly regioselective, one-pot double serial and double parallel displacements of the corresponding 2,4-bistriflates using azide and nitrite anions as nucleophiles. Alternatively, regioselective monotriflation at O2, O3, and O4 of l-rhamnose/l-fucose allowed selective inversions at respective positions leading to diverse rare sugars. The orthogonally protected deoxy amino l-sugar building blocks could be stereoselectively assembled to obtain biologically relevant bacterial O-glycans, as exemplified by the first total synthesis of the amino linker-attached, conjugation-ready tetrasaccharide of O-PS of Yersinia enterocolitica O:50 strain 3229 and the trisaccharide of Pseudomonas chlororaphis subsp. aureofaciens strain M71.
Stereoselective synthesis of a sulfated tetrasaccharide corresponding to a rare sequence in the galactofucan isolated from Sargassum polycystum
Zhou, Jun,Yang, Liping,Hu, Wenhao
, p. 4718 - 4726 (2014/06/09)
The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic str
Concise synthesis of the repeating units of the cell wall lipopolysaccharide of azospirillum brasilense SR80
Mandal, Pintu Kumar,Dhara, Debashis,Misra, Anup Kumar
, p. 1947 - 1953 (2014/07/22)
Syntheses of trisaccharide and tetrasaccharide repeating units of the cell wall lipopolysaccharide of Azospirillum brasilense SR80 as their 4-methoxyphenyl (PMP) glycosides have been achieved following a sequential glycosylation strategy in good yield. All intermediate steps are high-yielding and the glycosylation steps are highly stereoselective. Georg Thieme Verlag Stuttgart New York.
