- Regio/Stereoselective Glycosylation of Diol and Polyol Acceptors in Efficient Synthesis of Neu5Ac-α-2,3-LacNPhth Trisaccharide
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A concise approach to a Neu5Ac-α-2,3-LacNPhth trisaccharide derivative was developed. First, the regio/stereoselective glycosylation between glycoside donors and glucoNPhth diol acceptors was investigated. It was found that the regioselectivity depends not only on the steric hindrance of the C2-NPhth group and the C6-OH protecting group of the glucosamine acceptors, but also on the leaving group and protecting group of the glycoside donors. Under optimized conditions, LacNPhth derivatives were synthesized in up to 92 % yield through a regio/stereoselective glycosylation between peracetylated-α-galactopyranosyl trichloroacetimidate and p-methoxyphenyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-d-glucopyranoside, avoiding the formation of glycosylated orthoesters and anomeric aglycon transfer. Then, the LacNPhth derivative was deacylated and then protected on the primary position by TBDPS to form a LacNPhth polyol acceptor. Finally, the Neu5Ac-α-2,3-LacNPhth derivative was synthesized in 48 % yield through the regio/stereoselective glycosylation between the LacNPhth polyol acceptor and a sialyl phosphite donor. Starting from d-glucosamine hydrochloride, the target Neu5Ac-α-2,3-LacNPhth derivative was synthesized in a total yield of 18.5 % over only 10 steps.
- Zhang, Ying,Zhao, Fu-Long,Luo, Tao,Pei, Zhichao,Dong, Hai
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p. 223 - 234
(2018/12/05)
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- SYNTHETIC OLIGOSACCHARIDES FOR STAPHYLOCOCCUS VACCINE
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The present invention synthetic oligo-β-(1→6)-glucosamine structures and a methodology which essentially allows for the synthesis of any oligo-β-(1→6)-glucosamine species having a definite number of monosaccharide units, including a set pattern of acetylated and non- acetylated residues. The invention further provides antibodies to these synthetic oligo-β-(1→6)-glucosamines as well as compositions thereof and methods for treating and preventing infections caused by bacteria expressing poly-β-(1→6)-glucosamines, such as Staphylococcus aureus.
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- SYNTHETIC OLIGOSACCHARIDES FOR STAPHYLOCCOCUS VACCINE
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The present invention synthetic oligo-β-(1→6)-glucosamine structures and a methodology which essentially allows for the synthesis of any oligo-β-(1→6)- glucosamine species having a definite number of monosaccharide units, including a set pattern of acetylated and non-acetylated residues. The invention further provides antibodies to these synthetic oligo-β-(1→6)-glucosamines as well as compositions thereof and methods for treating and preventing infections caused by bacteria expressing poly-β-(1→6)-glucosamines, such as Staphylococcus aureus.
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- Synthesis and conformational analysis of 6-C-methyl-substituted 2-acetamido-2-deoxy-β-D-glucopyranosyl mono- and disaccharides
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(Chemical Equation Presented). Several 6-C-substituted 2-acetamido-2-deoxy- β-D-glucopyranosides (β-D-GlcNAc monosaccharides 1a-3a and 1,4-linked disaccharides 1b-3b) were studied by solution NMR spectroscopy. Conformational analysis of the (6S)- and (6R)
- Achkar, Jihane,Sanchez-Larraza, Isabel,Johnson, Carol A.,Wei, Alexander
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p. 214 - 226
(2007/10/03)
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- β-1,4-Galactosyltransferase-catalyzed synthesis of the branched tetrasaccharide repeating unit of Streptococcus pneumoniae Type 14
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A chemoenzymatic approach is described towards the branched tetrasaccharide repeating unit, β-d-Galp-(14)-β-d-Glcp-(16)-[β-d-Galp-(14)]-β-d-GlcpNAc, of Streptococcus pneumoniae type 14 in a form suitable for conjugation. The linear trisaccharide acceptor,
- Niggemann, Jutta,Kamerling, Johannis P.,Vliegenthart, Johannes F. G.
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p. 1605 - 1612
(2007/10/03)
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- Chemical Synthesis of Nod-Rm-1: the Nodilation Factor Involved in Rhizobium meliloti-legume Symbiosis
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A total synthesis of the sulfated lipotetrasaccharide (NodRm-1) is described.First, the disaccharide glycosyl donor - O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride 3a or
- Wang, Lai-Xi,Li, Chuan,Wang, Qin-Wei,Hui, Yong-Zheng
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p. 621 - 628
(2007/10/02)
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