The synthesis of derivatives of lactosamine and cellobiosamine to serve as probes in studies of the combining site of the monoclonal anti-I Ma antibody

Wong, Ting C.; Lemieux, R. U.

doi:10.1139/v84-197

Cited by 12 publications

(1 citation statement)

References 8 publications

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“…This conformational deviation appears to be the result of steric congestion caused by the 2-(benzoy1oxy)imino and the p-anomeric substituents, since it is observed similarly in some simple P-glycosides derived from 5l0) yet is absent in the respective P-ulosides (e.g. 7) or in the corresponding cl-anomers.…”

Section: Synthesis Of Galactosyl-p(1+4)-mannosyl-~( 1 -+ 6)-galactosementioning

confidence: 86%

A Facile Access to Trisaccharides with Central β‐D‐Mannose, α‐D‐Glucosamine, and β‐D‐Mannosamine Units

Lichtenthaler

Kaji

1985

Liebigs Ann. Chem.

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An expedient synthesis of the trisaccharides @-D-Galp-(1-+4)-P-D-Manp-(l-+6)-~-Gal (8), P-D-Galp-( 1 -+4)-@-~-ManpNAc-(l-+6)-~-Gd (ll), and @-D-Galp-( 1 -+4)-a-~-GlcpNAc-(1 -+6)-~-Gal(l2) is achieved utilizing the readily accessible lactose-derived building blocks hexa-0-benzoyl-a-D-lactosulosyl bromide (4) and its 2-(benzoyloxy)imino analogue 5 as glycosyl donors and 1,2: 3,4-di-O-isopropylidene-~-gdactose (6) as the acceptor. Stereocontrolled a-(silver triflate) and @-glycosidations (silver carbonate) were as smoothly effected as the subsequent, essentially stereospecific reductions of 0x0 (NaBH4) and (benzoy1oxy)-imino functions (diborane). The overall yields of 55-60% attainable for 4 -+ 8 and 5 -+ 11/ 12 render this disaccharide-derived building block approach highly effective for the construction of oligosaccharides with interior @-D-Man, @-D-ManNAc, and a-D-GlcNAc units. Ein einfacher Zugang zu Trisacchariden mit zentraler @A4annose-, a-mGlucosaminund PD-Mannosamin-EinheitEine effIziente Synthese der Trisaccharide P-D-Galp-(I -+4)-P-~-Manp-(l-+6)-~-Gal (8),12) gelingt unter Verwendung der aus Lactose leicht zuganglichen Disaccharid-Syntheseblocks Hexa-0-benzoyl-a-n-lactosulosyl-bromid (4) und seinem 2-(Benzoy1oxy)imino-Analogen 5 als Glycosyl-Donor und 1,2 : 3,4-Di-O-isopropyliden-~-galactose (6) als Acceptor. Stereokontrollierte a-(Silbertriflat) und @-Glycosidierungen (Ag2C0,) lieBen sich ebenso durchfuhren wie die nachfolgenden, nahezu stereospezifisch verlaufenden Reduktionen der 0x0-(NaBH4) und (Benzoy1oxy)imino-Funktionen (Diboran). Erreichbare Gesamtausbeuten von 55 -60% fur 4 -+ 8 und 5 ---* 11 bzw. 12 machen diesen DisaccharidSyntheseblock-Zugang zu einem der efizientesten fur den Aufbau von Oligosacchariden mit inneren P-D-Man-, P-D-ManNAc-und a-D-GlcNAc-Einheiten.The presently prevailing approach towards the synthesis of biologically important oligosaccharides comprises their stepwise construction from suitably blocked, anomerically activated glycosyl donor and a monosaccharide acceptor with a free hydroxy group'! This well-elaborated methodology, however, results in the extension of a saccharide by more than one sugar unit only if the di-or oligosaccharide components required were presynthesized from the constituent monosaccharide units 1,2). In contrast, the synthetic potential inherent in the common in large scale available disaccharides has been tapped comparatively little, scant examples being the lactose-derived lactosaminyl donors 23-6) and some analogues prepared from cellobiose7) and maltose *I. The acquisition of these building blocks 0 VCH Verlagsgesellschaft mbH, D-6940 Weinheim, 1985

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Section: Synthesis Of Galactosyl-p(1+4)-mannosyl-~( 1 -+ 6)-galactosementioning

confidence: 86%

A Facile Access to Trisaccharides with Central β‐D‐Mannose, α‐D‐Glucosamine, and β‐D‐Mannosamine Units

Lichtenthaler

Kaji

1985

Liebigs Ann. Chem.

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Enantiopure D-, L- (and 2-epi-) Purpurosamine C-Type Glycosyl Donors from Racemic Acrolein Dimer − Biocatalytic Resolution

et al. 1998

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Both enantiomers of purpurosamine C‐type glycosyl donors [(ent)‐9, (ent)‐10, (ent)‐11] and of a 2‐azido epimer [(ent)‐14] with a modified pattern of protecting groups have been prepared from racemic 3,4‐dihydro‐2H‐pyran‐2‐carbaldehyde (acrolein dimer, rac‐1, “indirect aziridination”, “azidonitration”). In two cases (rac‐23β: methyl 6‐O‐acetyl‐2,3,4‐trideoxy‐2α‐trifluoroacetylamino‐β‐D/L‐hexopyranoside, rac‐32: methyl 6‐O‐acetyl‐2β‐azido‐2,3,4‐trideoxy‐β‐D/L‐hexopyranoside), efficient resolution has been achieved biocatalytically.

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Characterization of inhibitory activities and binding mode of synthetic 6′-modified methyl N-acetyl-β-lactosaminide toward rat liver CMP-d-Neu5Ac: d-galactoside-(2 → 6)-α-d-sialyltransferase

Kajihara

Kodama

Wakabayashi

et al. 1993

Carbohydrate Research

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The synthesis of derivatives of lactosamine and cellobiosamine to serve as probes in studies of the combining site of the monoclonal anti-I Ma antibody

Cited by 12 publications

References 8 publications

A Facile Access to Trisaccharides with Central β‐D‐Mannose, α‐D‐Glucosamine, and β‐D‐Mannosamine Units

A Facile Access to Trisaccharides with Central β‐D‐Mannose, α‐D‐Glucosamine, and β‐D‐Mannosamine Units

Enantiopure D-, L- (and 2-epi-) Purpurosamine C-Type Glycosyl Donors from Racemic Acrolein Dimer − Biocatalytic Resolution

Characterization of inhibitory activities and binding mode of synthetic 6′-modified methyl N-acetyl-β-lactosaminide toward rat liver CMP-d-Neu5Ac: d-galactoside-(2 → 6)-α-d-sialyltransferase

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