Synthesis and solution conformation of the type 2 blood group oligosaccharide. cap alpha. LFuc(1. -->. 2). beta. DGal(1. -->. 4). beta. DGlcNAc

Journal Article · Tue Mar 16 04:00:00 EST 1982 · Biochemistry; (United States)

OSTI ID:7071803

Rosevear, P R ^[1]; Nunez, H A; Barker, R

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1. Michigan State Univ., East Lansing

Partially purified glycosyltransferases and chemically synthesized sugar nucleotides have been used to prepare a number of oligosaccharides related to the type 2 (human) blood group (H) substance. The following oligosaccharides were prepared and purified by ion-exchange and gel-filtration chromatography: ..cap alpha..LFuc(1..-->..2)-..beta..DGal(1..-->..4)..beta..DGlcNAc-hexanolamine, ..cap alpha..LFuc(1..-->..2)..beta..D(1-/sup 13/C)Gal(1..-->..4)..beta..DGlcNAc-hexanolamine, ..cap alpha..L(1-/sup 13/C)Fuc(1..-->..2)..beta..D(1-/sup 13/C)Gal(1..-->..4)..beta..DGlcNAc-hexanolamine, ..cap alpha..L(1-/sup 13/C)-Fuc(1..-->..2)..beta..D(1-/sup 13/C)Gal(1..-->..4)..beta..DGlcNAc, ..cap alpha..LFuc(1..-->..2)..beta..D-(1-/sup 13/C)Gal(1..-->..4)..beta..DGlcNAc, ..cap alpha..L(1-/sup 13/C)Fuc(1..-->..2)..beta..D(1-/sup 13/C)-Gal(1..-->..4)..beta..DGlc, ..cap alpha..LFuc(1..-->..2)..beta..D(1-/sup 13/C)Gal-hexanolamine, ..cap alpha..L(1-/sup 13/C)Fuc(1..-->..2)..beta..D(1-/sup 13/C)Gal-ethanol, ..cap alpha..LFuc(1..-->..2)..beta..D-(1-/sup 13/C)Gal-ethanol, ..cap alpha..L(1-/sup 13/C)Fuc(1..-->..2)..beta..DGal-ethanol and ..cap alpha..LFuc(1..-->..2)..beta..D(2-/sup 13/C)Gal-ethanol. Specific /sup 13/C enrichment and comparison with /sup 13/C-enriched model compounds allowed unambiguous assignment of /sup 13/C resonances. Fucosylation at O2 of ..beta..DGal(1..-->..4)..beta..DGlcNAc-hexanolamine caused a 5.6 ppm downfield shift of the C2 resonance of Gal. Fucosylation of the disaccharide ..beta..DGal(1..-->..4)DGlcNAc resulted in a similar pattern of chemical shift changes. Interresidue coupling constants (/sup 3/J/sub C1-C1'/ approx. = 1.5 Hz observed as line broadening, /sup 3/J/sub H1-C2'/ approx. = 3.2 Hz, /sup 3/J/sub C1'-C3''/ approx. = 0 Hz, /sup 3/J/sub C1'-C5''/ approx. = 1.0 Hz observed as line broadening, and /sup 2/J/sub C1'-C4''/ approx. = 1.5 Hz) in the enriched oligosaccharides allowed estimation of the most abundant conformer for the Phi and Psi torsion angles in the ..beta..DGal(1..-->..4)GlcNAc (Phi' approx. = 60/sup 0/ and Psi' approx. = 15/sup 0/) and ..cap alpha..LFuc(1..-->..2)DGal(Phi approx. = 55/sup 0/ and Psi approx. = 0/sup 0/) glycosidic linkages of the trisaccharide. (JMT)

• OSTI ID: 7071803
• Journal Information: Biochemistry; (United States), Journal Name: Biochemistry; (United States) Vol. 21:6; ISSN BICHA
• Country of Publication: United States
• Language: English

Related Subjects

550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
BLOOD GROUPS
CARBOHYDRATES
CARBON 13
CARBON ISOTOPES
ENZYMES
EVEN-ODD NUCLEI
ISOTOPE APPLICATIONS
ISOTOPES
LABELLED COMPOUNDS
LIGHT NUCLEI
MAGNETIC RESONANCE
MOLECULAR STRUCTURE
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUCLEOTIDES
OLIGOSACCHARIDES
ORGANIC COMPOUNDS
RESONANCE
SACCHARIDES
STABLE ISOTOPES
SYNTHESIS
TRACER TECHNIQUES
TRANSFERASES