177358-21-3Relevant academic research and scientific papers
Synthesis of lactosamine-based building blocks on a practical scale and investigations of their assembly for the preparation of19F-labelled LacNAc oligomers
Romanò, Cecilia,Oscarson, Stefan
, p. 2265 - 2278 (2019)
The ubiquitous disaccharide N-acetyllactosamine (LacNAc type 2, Galβ1,4GlcNAc) is often over-expressed on the surface of cancer cells where it is bound by tumour secreted galectins contributing to cancer-related processes such as metastasis, adhesion, tumour survival, and immune escape. To facilitate NMR investigations into the binding interactions between oligo-LacNAc structures and galectins, which can show both exo- and endo-binding behaviour, a library of regioselectively 19F-labelled oligo-LacNAc structures was required. Herein, the synthesis on a practical scale of various N-protected (Troc, Phth, TFAc) lactosamine donors is reported starting from commercially available lactosamine hydrochloride. Investigations into their glycosylations with lactosamine acceptors to form 19F-containing LacNAc oligomers showed that benzylated acceptors significantly improved the yields over acetylated ones, and that, gratifyingly, the almost untried N-trifluoroacetamide (NTFAc) protected donors, already containing the desired 19F-label, were found to be optimal, both considering reaction yields and purification of the glycosylation reactions. The NTFAc group of reducing end acceptors was introduced through N-amide transacylation of linker-equipped LacNAc structures. A [2 + 2] synthetic approach was optimized for the preparation of tetrasaccharide LacNAc/TFAc-dimers and also further expanded to the synthesis of hexasaccharide LacNAc/TFAc-trimer structures.
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 the Sda determinant and two analogous tetrasaccharides.
van Seeventer,Kamerling,Vliegenthart
, p. 181 - 195 (2007/10/03)
To contribute to the possibility of studying in greater detail the biological significance of Sda-containing glycans as occur in Tamm-Horsfall glycoprotein, the following three spacer-linked tetrasaccharides have been synthesized: the Sda determinant alpha-Neu p5Ac-(2-->3)-[beta- D-GalpNAc-(1-->4)]-beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->O)(CH2)5NH 2 (1), the Gal-analogue alpha-Neup5Ac-(2-->3)-[beta-D-Galp-(1-->4)]-beta-D-Galp-(1-->4) -beta-D-GlcpNAc-(1-->O)(CH2)5NH2 (2), and the GlcNAc-analogue alpha-Neup5Ac-(2-->3)-[beta-D-GlcpNAc-(1-->4)]- beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->O)(CH2)5NH2 (3). The general trisaccharide acceptor 5-azidopentyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy- D-glycero-alpha-D-galactonon-2-ulopyranosylonate)-(2-->3)-(2 ,6-di-O-benzyl- beta-D-galactopyranosyl)-(1-->4)-3,6-di-O- benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside was prepared, using methyl (phenyl 5- acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto- non- 2-ulopyranosid)- onate as the sialyl donor. For the syntheses of 1, 2, and 3 the glycosyl donors 3,4,6-tri-O- acetyl-2-deoxy-2-phthalimido-alpha-D-galactopyranosyl bromide, 2,3,4,6-tetra-O-acetyl-alpha-D- galactopyranosyl bromide, and 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido -beta-D-glucopyranosyl trichloroacetimidate, respectively, proved to be the most suitable.
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.
