Synthesis of 3,6-Di-O-(alpha-D-mannopyranosyl)-D-mannose.

Arnarp, Jan; Lōnngren, Jörgen; McCoy, Kim E.

doi:10.3891/acta.chem.scand.32b-0696

Cited by 43 publications

(14 citation statements)

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“…The following synthetic oligosaccharides were used in the study: (25)(26)(27)(28)(29). The corresponding sugar alcohols were prepared by sodium borohydride reduction.…”

mentioning

confidence: 99%

Mitogenic leukoagglutinin from Phaseolus vulgaris binds to a pentasaccharide unit in N-acetyllactosamine-type glycoprotein glycans.

Hammarström¹,

Hammarström²,

Sundblad³

et al. 1982

Proc. Natl. Acad. Sci. U.S.A.

132

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The carbohydrate binding specificity of leukoagglutinin (La; Phaseolus vulgaris isolectin L4) was studied by using quantitative precipitation and precipitation-inhibition. A series of purified glycopeptides and synthetic oligosaccharides were used as inhibitors. The minimal structural unit required for La binding was the disaccharide GlcNAc(1-+2)Man. Additions for this basic unit of different sugar residues gave a positive or negative contribution to binding. The most complementary structure was the pentasaccharide Gal(1-.>4)GlcNAc(1-*2)Man 6 Gal(1-*4)GlcNAc. This pentasaccharide unit occurs in tetraantennary N-acetyllactosamine-type glycoprotein glycans. Glycoproteins containing such structures were accordingly precipitated by La. Selected glycopeptides and oligosaccharides were also tested as inhibitors of La-induced DNA synthesis in human lymphocytes. The pattern of inhibition was essentially the same as that obtained by precipitation-inhibition, indicating that binding to lymphocytes via the carbohydrate binding site of the lectin is an essential step in the activation process.

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“…The following synthetic oligosaccharides were used in the study: (25)(26)(27)(28)(29). The corresponding sugar alcohols were prepared by sodium borohydride reduction.…”

mentioning

confidence: 99%

Mitogenic leukoagglutinin from Phaseolus vulgaris binds to a pentasaccharide unit in N-acetyllactosamine-type glycoprotein glycans.

Hammarström¹,

Hammarström²,

Sundblad³

et al. 1982

Proc. Natl. Acad. Sci. U.S.A.

132

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“…Branching at 0 -3 and 0-6 of galacto-and manno-pyranosides occurs in blood-group substances (12) and glycoproteins (13). Compared with these hexoses, glucose lacks an axial-equatorial vicinal diol system that may be exploited to generate the required substitution pattern of blocking groups (14)(15)(16). A solution to this problem is described here, which facilitated the synthesis of two biologically important branched structures.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of the colitose determinant of Escherichiacoli O111 and 3,6-di-O-(α-D-galactopyranosyl)-α-D-glucopyranoside

Iversen¹,

Bundle²

1982

Can. J. Chem.

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TOMMY IVERSEN and DAVID R. BUNDLE. Can. J. Chem. 60, 299 (1982). The syntheses of two branched trisaccharides, which constitute important elements of enterobacterial lipopolysaccharides are described. The common structural feature of each trisaccharide is a-D-glucopyranoside, upon which branching occurs at the 0 -3 and 0 -6 positions. Selective blocking of this hexoside at 0 -2 and 0-4 by persistent blocking groups was accomplished by benzylation of 1 ,6-anhydro-P-D-glucopyranoside (1). Acetolysis of the product 2 afforded a mixture of anomeric triacetates 3 from which the corresponding 3,6-di-0-acetyI-2,4-O-benzyl-a-~-glucopyranosyl chloride (4) was prepared. The a and P 8-methoxycarbonyloctyl glycosides 5 and 6 were obtained in the ratio -2:1, when 4 was reacted with 8-methoxycarbonyloctanol. Transesterification of the a-glycoside 5 gave the aglyconic intermediate 7 from which each trisaccharide could be obtained in a one step reaction. Thus glycosylation of 7 with tetra-0-benzyl-a-D-galactopyranosyl chloride (8) or 2,4-di-0-benzyl-3,6-dideoxy-a-Lxylo-hexopyranosyl chloride (10) gave the trisaccharides 11 and 13. In both cases removal of blocking groups was achieved in a single hydrogenolysis step. Trisaccharide 12 represents a trisaccharide sequence present in the core saccharide of Salmonella lipopolysaccharides, while the colitose containing trisaccharide 14 is an essential element of the E. coli 011 1 0-antigen.TOMMY IVERSEN et DAVID R. BUNDLE. Can. J . Chem. 60, 299 (1982).On decrit la synthese de deux trisaccharides ramifies qui constituent des elements importants des lipopolysaccharides enterobacteriens. La caracteristique structurale commune a chaque trisaccharide est I'a-D-glucopyrannoside, sur lequel s'effectue les ramification en positions 0-3 et 0-6. On a p11 proteger selectivement cet hexoside en positions 0 -2 et 0 -4 a I'aide de groupes protecteurs tres stables en benzylant I'anhydro-1,6 P-D-glucopyrannose (I). L'acelotyse du compose 2 conduit a un melange de triacetates 3 anomeres a partir duquel on a prepare le chlorure de di-0-acetyl-3,6 0-benzyl-2,4 a-D-glucopyrannosyle (4). On a obtenu les a -et P-glycosides de methoxycarbonyl-8 octyle, 5 et 6, dans un rapport de 2: 1 environ en faisant reagir le compose 4 avec le methoxycarbonyl-8 octanol. La transesterification de l'a-glycoside conduit al'intermediaire aglyconique 7 a partir duquel on peut obtenir chaque trisaccharide en une seule etape. Ainsi la glycosilation du compose 7 par le chlorure de tetra-0-benzyl a-D-galactopyrannosyle (8) ou par le chlorure de di-0-benzyl-2,4 dideoxy-3,6 a-L-xylohexopyrannosyle (10) donne les trisaccharides 11 et 13. Dans les deux cas, I'hydrolyse permet d'effectuer la deprotection en une seule etape. Le trisaccharide 12 represente une suite de trisaccharides presents dans le noyau saccharique des lipopolysaccharides du type Salmonella, tandis que le trisaccharide 14 contenant la colitose est un element essentiel de I'antigene 0 de I'E. Coli 0 1 11.[Traduit par le journal] Introduction Although antigenic determ...

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“…Whilst several synthetic strategies to 2,4-di-O-protected mannosides are reported in the literature, [18][19][20] Kaur and Hindsgaul have developed a rapid synthesis of a structurally related analogue of the branched mannotrisaccharide 6 requiring no prior protection steps. 21 This strategy involved mannosylation of unprotected octyl b-D D-mannopyranoside with 2.5 equiv of donor sugar, giving a complex mixture of products.…”

Section: Resultsmentioning

confidence: 99%

“…Mp 88-90°C (EtOAc/hexane). 1 (19). To a soln of acetal 18 (100 mg, 0.16 mmol), 4 Å molecular sieves (100 mg), and trimethylamine borane (60 mg, 0.81 mmol) in CH 2 Cl 2 (6 mL) at 0°C was added dropwise a suspension of aluminum trichloride (87 mg, 0.65 mmol) in Et 2 O (3 mL).…”

Section: General Methodsmentioning

confidence: 99%

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The synthesis of a series of modified mannotrisaccharides as probes of the enzymes involved in the early stages of mammalian complex N-glycan formation

Tarling

Withers

2004

Carbohydrate Research

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Synthesis of 3,6-Di-O-(alpha-D-mannopyranosyl)-D-mannose.

Cited by 43 publications

References 0 publications

Mitogenic leukoagglutinin from Phaseolus vulgaris binds to a pentasaccharide unit in N-acetyllactosamine-type glycoprotein glycans.

Mitogenic leukoagglutinin from Phaseolus vulgaris binds to a pentasaccharide unit in N-acetyllactosamine-type glycoprotein glycans.

Synthesis of the colitose determinant of Escherichiacoli O111 and 3,6-di-O-(α-D-galactopyranosyl)-α-D-glucopyranoside

The synthesis of a series of modified mannotrisaccharides as probes of the enzymes involved in the early stages of mammalian complex N-glycan formation

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