816451-36-2Relevant articles and documents
High-efficiency synthesis of chitooligosaccharides
Huang, Gangliang
scheme or table, p. 70 - 72 (2012/04/23)
The solid-phase synthesis of chitooligosaccharides is described. After the NHCbz trichloroacetimidate donors 6 and 14 were synthesized; solid-phase synthesis was performed using the Wang resin as support. The illustrated tetra-Nacetyl- chitotetraose 1 was
Solid-phase synthesis of di-N-acetyl-β-chitobiosyl allosamizoline
Huang, Gangliang
scheme or table, p. 625 - 627 (2012/06/29)
The solid-phase synthesis of di-N-acetyl-β-chitobiosyl allosamizoline 2 was reported. After the 6-O-benzyl allosamizoline 16, NHCbz trichloroacetimidate donors 7, and 14 were synthesized; solid-phase synthesis was performed using the Wang resin as support. The target di-N-acetyl-β- chitobiosyl allosamizoline 2 was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively.
Solid-phase synthesis of Di-N-Acetyl-β-chitobiosyl NAG-thiazoline
Huang, Gangliang,Chen, Ya
scheme or table, p. 649 - 651 (2012/05/20)
The solid-phase synthesis of di-N-acetyl-β-chitobiosyl NAG (N-acetyl D-glucosamine)-thiazoline 3 was reported. After the 6-O-benzyl NAG-thiazoline 9, NHCbz trichloroacetimidate donors 14, and 21 were synthesized, and solid-phase synthesis was performed using the Wang resin as support. The target di-N-acetyl-β-chitobiosyl NAGthiazoline 3 was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively. donors, Wang resin, Glycosylation reactions.
Towards a modular synthesis of well-defined chitooligosaccharides: Synthesis of the four chitodisaccharides
Barroca-Aubry, Nadine,Pernet-Poil-Chevrier, Astrid,Domard, Alain,Trombotto, Stéphane
experimental part, p. 1685 - 1697 (2010/10/19)
The total chemical synthesis of the four well-defined chitodisaccharides is described using N-trichloroacetyl (TCA) and N-benzyloxycarbonyl (Z) as C-2 protecting groups for acetamido and free amino groups, respectively. The synthesis is carried out accord
Systematic synthesis of bisubstrate-type inhibitors of TV- acetylglucosaminyltransferases
Hanashima, Shinya,Inamori, Kei-Ichiro,Manabe, Shino,Taniguchi, Naoyuki,Ito, Yukishige
, p. 3449 - 3462 (2008/02/03)
Bisubstrate-type inhibitors for N-acetylglucosaminyltransferase (GnT)-V and -IX were designed and synthesized. These compounds carry both an acceptor trisaccaride and an UDP-GlcNAc component tethered by a linker of variable length. The acceptor trisaccharide unit was constructed using a combination of a polymer support and a resin capture-release strategy. Namely, starting with a β-mannoside bound to low molecular weight monomethyl PEG (MPEG), successive glycosylations with donors having chloroacetyl group produced the trisaccharide, which was subjected to the capture-release purification using cysteine loaded resin. UDP-GlcNAc units carrying phosphate moieties were separately synthesized from the bromoacetamide-containing glucosamine derivative. Ligation between the acceptor thiol and each alkyl bromide on the donor unit readily proceeded, and produced the coupling product. The introduction of the UMP component gave target compounds. All of the synthesized compounds had significant activities to GnT-V and -IX. Their potencies were dependent upon the linkers length. GnT-IX was more sensitive to these inhibitors and optimum linker length was clearly different between these GnTs. The most potent inhibitor of GnT-V had Ki = 18.3 μM, while that of GnT-IX had Ki = 4.7 μM.
Synthesis of a bisubstrate-type inhibitor of N- acetylglucosaminyltransferases
Hanashima, Shinya,Manabe, Shino,Inamori, Kei-Ichiro,Taniguchi, Naoyuki,Ito, Yukishige
, p. 5674 - 5677 (2007/10/03)
Transfer interference: Synthesis of the bisubstrate-type N-acetylglucosaminyltransferase (GnT) inhibitor 1 was achieved by a polymer-resin hybrid capture-release strategy for the construction of the acceptor component. One-pot ligation in aqueous media pr
