177358-22-4Relevant academic research and scientific papers
A facile synthesis of sialylated oligolactosamine glycans from lactose via the Lafont intermediate
Peng, Peng,Liu, Han,Gong, Jianzhi,Nicholls, John M.,Li, Xuechen
, p. 3634 - 3639 (2014/08/18)
The 2-aminophosphonium iodide lactosamine glycoside (Lafont intermediate) readily obtained from lactose has been previously shown not to be amenable to derivatization for oligosaccharide synthesis, but has now been successfully converted via the salicylaldehyde imine into suitably protected lactosamine building blocks (13-16) for glycosylation. The titled strategy has enabled us to rapidly synthesize the Neu5Ac-α-2,3LacNAc-β-1,3LacNAc pentasaccharide and Neu5Ac-α-2,3LacNAc-β-1,3LacNAc-β-1,3LacNAc heptasaccharide. Furthermore, this strategy has been adopted for the synthesis of other 2-amino sugars (e.g., 23-27), which provides a useful method for the preparation of 2-amino sugar building blocks.
Toward fully synthetic homogeneous β -human Follicle-Stimulating hormone (β -hFSH) with a biantennary N-linked dodecasaccharide. synthesis of β -hFSH with chitobiose units at the natural linkage sites
Nagorny, Pavel,Fasching, Bernhard,Li, Xuechen,Chen, Gong,Aussedat, Baptiste,Danishefsky, Samuel J.
supporting information; experimental part, p. 5792 - 5799 (2009/09/24)
A highly convergent synthesis of the sialic acid-rich biantennary N-linked glycan found in human glycoprotein hormones and its use in the synthesis of a fragment derived from the β -domain of human Follicle-Stimulating Hormone (hFSH) are described. The synthesis highlights the use of the Sinay radical glycosidation protocol for the simultaneous installation of both biantennary side-chains of the dodecasaccharide as well as the use of glycal chemistry to construct the tetrasaccharide core in an efficient manner. The synthetic glycan was used to prepare the glycosylated 20-27aa domain of the β -subunit of hFSH under a Lansbury aspartylation protocol. The proposed strategy for incorporating the prepared N-linked dodecasaccharide-containing 20-27aa domain into β -hFSH subunit was validated in the context of a model system, providing protected β -hFSH subunit functionalized with chitobiose at positions 7 and24.
Synthesis of the fucosylated biantennary N-glycan of erythropoietin
Wu, Bin,Hua, Zihao,Warren, J. David,Ranganathan, Krishnakumar,Wan, Qian,Chen, Gong,Tan, Zhongping,Chen, Jiehao,Endo, Atsushi,Danishefsky, Samuel J.
, p. 5577 - 5579 (2007/10/03)
A synthesis of the protected biantennary N-glycan of the naturally occurring glycoprotein, erythropoietin, is described.
Synthesis of a hexasaccharide corresponding to a porcine zona pellucida fragment that inhibits porcine sperm-oocyte interaction in vitro
Spijker, Nynke M.,Keuning, Cor A.,Hooglugt, Mariska,Veeneman, Gerrit H.,Van Boeckel, Constant A. A.
, p. 5945 - 5960 (2007/10/03)
The synthesis of hexasaccharide 1, [galβ(1-4)GlcNAc[6OSO3]β(1-3)Galβ(1-4)GlcNAcβ(1-3)Galβ(1-3)GalNA cα-O(CH2)3NH2], which corresponds to a porcine zona pellucida fragment that inhibits porcine sperm-oocyte interaction, is described. Compound 1 was obtained from fully protected hexasaccharide 2, which was in turn constructed from protected Galβ(1-3)GalNAc disaccharide 5, containing an α-linked 3-azidopropyl spacer, and from lactosamine derivatives 3 and 4. Disaccharide 3 and 4 were prepared by coupling of selenophenyl glycoside 6 with glycosyl acceptors containing anomeric thioethyl groups. NIS/TfOH promoted coupling of disaccharide 4 with 5 afforded 29, which was transformed into the tetrasaccharide acceptor 30 by selective removal of the levulinoyl group. Glycosylation of 30 with 3 afforded protected hexasaccharide 2. Removal of the phthalimido groups, acetylation, followed by selective removal of the allyl group and sulphation, and finally complete deprotection afforded hexasaccharide 1.
