The chemical synthesis of O-α-l-fucopyranosyl-(1→2)-O-β-d-galactopyranosyl-(1→3)-O-[α-l-fucopyranosyl-(1→4)]-2- acetamido-2-deoxy-d-glucopyranose, the lewis b blood-group antigenic determinant

Rana, Surjit S.; Barlow, Joseph J.; Matta, Khushi L.

doi:10.1016/s0008-6215(00)81873-x

Cited by 33 publications

(10 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Again, these yields are almost identical to the yield obtained for fucosylation of Le a . Compound 14 was converted to 15 in a manner analogous to that used for Le a (Scheme , 9 to 10 ) and then saponified to produce Le b ( 2 ) which correlated with the reported data 4c…”

Section: Resultssupporting

confidence: 68%

“…We have used the sulfoxide glycosylation method to make all the glycosidic linkages in the Lewis blood group antigens Le a , Le b , and Le x . Our syntheses are comparable to the best syntheses of these molecules. − Given the demonstrated predictability of the sulfoxide glycosylation reaction for this family of oligosaccharides, it should be possible to make other members of the Lewis blood group family as well as analogues without having each synthesis turn into a new problem that must be solved by experimenting with different reaction conditions or glycosylation methods.…”

Section: Discussionmentioning

confidence: 81%

“…The Lewis blood group antigens are a biologically important family of oligosaccharides (Figure ) that have attracted the attention of numerous synthetic carbohydrate groups because of their structural complexity. − They are branched oligosaccharides containing both α and β linkages to hindered secondary alcohols. Each blood group antigen has been synthesized several times previously.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Generalizing Glycosylation: Synthesis of the Blood Group Antigens Le^a, Le^b, and Le^x Using a Standard Set of Reaction Conditions

1996

View full text Add to dashboard Cite

Because there are no general reaction conditions for any glycosylation method, biologically interesting oligosaccharides can only be made in a small number of laboratories in the world. To make carbohydrate synthesis accessible to nonspecialists, it is critical to have glycosylation methods that will work in a wide range of cases under a single set of conditions. The Lewis blood group antigens have attracted the attention of numerous synthetic carbohydrate groups because of their structural complexity. Although they have been synthesized many times, they have never been made using a single glycosylation method under one set of reaction conditions. In this paper, we show that the sulfoxide glycosylation method can be used to form all of the glycosidic linkages in the Lewis blood group antigens Lea (1), Leb (2), and Lex (3) stereoselectively under a uniform set of reaction conditions. This work highlights the flexibility of the sulfoxide method and demonstrates its utility for constructing families of related oligosaccharides.

show abstract

Section: Resultssupporting

confidence: 68%

Section: Discussionmentioning

confidence: 81%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Generalizing Glycosylation: Synthesis of the Blood Group Antigens Le^a, Le^b, and Le^x Using a Standard Set of Reaction Conditions

1996

View full text Add to dashboard Cite

show abstract

“…Therefore, we searched for a better route to 1a. Previously, the glycosidation reaction to a disaccharide derivative (5) has been performed with methyl (2,3,4-tri-O-acetyl-R-Dglucopyranosyl bromide)uronate 51 and benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (4) 52 as a glycosyl donor and a glycosyl acceptor, respectively. The reaction provided the corresponding disaccharide (5) in a low yield of 29% due to a lower reactivity of the glycosyl donor bringing about multiple unknown byproducts.…”

Section: Resultsmentioning

confidence: 99%

Bottom-Up Synthesis of Hyaluronan and Its Derivatives via Enzymatic Polymerization: Direct Incorporation of an Amido Functional Group

et al. 2005

View full text Add to dashboard Cite

This paper reports the synthesis of hyaluronan (HA) and its derivatives via the hyaluronidase-catalyzed polymerization of 2-substituted oxazoline derivative monomers designed as "transition-state analogue substrates". Polymerization of 2-methyl oxazoline monomer from N-acetylhyalobiuronate (GlcAbeta(1-->3)GlcNAc) effectively proceeded at pH 7.5 and 30 degrees C, giving rise to synthetic HA (natural type) in an optimal yield of 78% via ring-opening polyaddition under total control of regioselectivity and stereochemistry. Hyaluronidase catalysis enabled the polymerization of 2-ethyl, 2-n-propyl, and 2-vinyl monomers, affording the corresponding HA derivatives (unnatural type) with N-propionyl, N-butyryl, and N-acryloyl functional groups, respectively, at the C2 position of all glucosamine units in good yields. The 2-isopropyl oxazoline derivative provided the N-isobutyryl derivative of HA in low yields. Monomers of 2-phenyl and 2-isopropenyl oxazoline derivatives were not polymerized. The mechanism of the polymerization is discussed.

show abstract

“…These include the A, B, H antigens [24][25][26], Lewis b [27,28], MN sialoglycoproteins [29,30], Sda [31,and Rh0 (D) …”

Section: Quantitation Of Specific Anti-leamentioning

confidence: 99%

A New Technique in Quantitative Immunohematology: Solid-Phase Kinetic Enzyme-Linked Immunosorbent Assay

Spitalnik¹,

Cowles²,

Cox³

et al. 1983

Vox Sanguinis

View full text Add to dashboard Cite

A solid-phase kinetic enzyme-linked immunosorbent assay has been developed to measure binding of antibodies to purified or synthetic blood group antigens and tested in the Lewis blood group system. Chemically synthesized Lewis α antigen is used as the target for the binding of serum antibody in this sandwich-type assay. Kinetic, rather than endpoint, determinations are used to calculate the amount of specific antibody. Data are presented showing the assay to be quantitative, sensitive, and specific. It can separately quantitate the amount of IgG or IgM anti-Lewis a present in patient sera. The assay uses commercially available reagents and is semiautomated. Thus, it will be useful for studies in quantitative immunohematology as other blood group antigens become available in purified form.

show abstract

The chemical synthesis of O-α-l-fucopyranosyl-(1→2)-O-β-d-galactopyranosyl-(1→3)-O-[α-l-fucopyranosyl-(1→4)]-2- acetamido-2-deoxy-d-glucopyranose, the lewis b blood-group antigenic determinant

Cited by 33 publications

References 21 publications

Generalizing Glycosylation: Synthesis of the Blood Group Antigens Le^a, Le^b, and Le^x Using a Standard Set of Reaction Conditions

Generalizing Glycosylation: Synthesis of the Blood Group Antigens Le^a, Le^b, and Le^x Using a Standard Set of Reaction Conditions

Bottom-Up Synthesis of Hyaluronan and Its Derivatives via Enzymatic Polymerization: Direct Incorporation of an Amido Functional Group

A New Technique in Quantitative Immunohematology: Solid-Phase Kinetic Enzyme-Linked Immunosorbent Assay

Contact Info

Product

Resources

About

The chemical synthesis of O-α-l-fucopyranosyl-(1→2)-O-β-d-galactopyranosyl-(1→3)-O-[α-l-fucopyranosyl-(1→4)]-2- acetamido-2-deoxy-d-glucopyranose, the lewis b blood-group antigenic determinant

Cited by 33 publications

References 21 publications

Generalizing Glycosylation: Synthesis of the Blood Group Antigens Lea, Leb, and Lex Using a Standard Set of Reaction Conditions

Generalizing Glycosylation: Synthesis of the Blood Group Antigens Lea, Leb, and Lex Using a Standard Set of Reaction Conditions

Bottom-Up Synthesis of Hyaluronan and Its Derivatives via Enzymatic Polymerization: Direct Incorporation of an Amido Functional Group

A New Technique in Quantitative Immunohematology: Solid-Phase Kinetic Enzyme-Linked Immunosorbent Assay

Contact Info

Product

Resources

About

Generalizing Glycosylation: Synthesis of the Blood Group Antigens Le^a, Le^b, and Le^x Using a Standard Set of Reaction Conditions

Generalizing Glycosylation: Synthesis of the Blood Group Antigens Le^a, Le^b, and Le^x Using a Standard Set of Reaction Conditions