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Convergent synthesis of tetra- and penta-saccharide fragments of dimeric Lewis X.

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Title: Convergent synthesis of tetra- and penta-saccharide fragments of dimeric Lewis X.
Authors: Forman, Adam1 (AUTHOR), Hendel, Jenifer1 (AUTHOR), Auzanneau, France-Isabelle1 (AUTHOR) fauzanne@uoguelph.ca
Source: Carbohydrate Research. Aug2019, Vol. 482, pN.PAG-N.PAG. 1p.
Subjects: Thiourea, Glycosylation, Epitopes, Fucosylation, Metals, Immunoglobulins
Abstract: The convergent synthesis of tetra- and penta-saccharide fragments of the TACA dimeric Lex is described. The synthetic strategy relied on the preparation of a protected GlcNTCA-(1,3)-Gal-(1,4)-GlcNAc trisaccharide diol free at O-3 of both glucosamine residues. Key steps in the preparation of this diol involved glycosylation at O-4 of N -acetylglucosamine using activation of a trichloroacetimidate with BF 3 · Et 2 O at 40 °C, removal of the non-reducing end O-3' chloroacetate with thiourea, and glycosylation with a N -trichloroacetamido glucosamine trichloroacetimidate donor. After conversion to the diol acceptor, the trisaccharide was selectively fucosylated at the nonreducing end under NIS/TMSOTf activation, or di-fucosylated under CuBr 2 /Bu 4 NBr activation. The protected tetra- and pentasaccharides were then efficiently deprotected under dissolving metal conditions and the nonreducing end glucosamine residues were N- acetylated during the reaction work up. The deprotected compounds will be used as soluble competitors to characterize the epitopes recognized by anti-polymeric Lex antibodies. Image 1 • Synthesis of tetra- and penta-saccharide fragments of dimeric Lex is described. • A trisaccharide diol free at O-3 of both glucosamine residues was prepared. • The trisaccharide diol was mono-fucosylated under NIS/TMSOTf activation. • The trisaccharide diol was di-fucosylated under CuBr 2 /Bu 4 NBr activation. • Tetra- and pentasaccharides were deprotected under dissolving metal conditions. [ABSTRACT FROM AUTHOR]
Copyright of Carbohydrate Research is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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DbLabel: Engineering Source
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Items – Name: Title
  Label: Title
  Group: Ti
  Data: Convergent synthesis of tetra- and penta-saccharide fragments of dimeric Lewis X.
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  Data: <searchLink fieldCode="AR" term="%22Forman%2C+Adam%22">Forman, Adam</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Hendel%2C+Jenifer%22">Hendel, Jenifer</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Auzanneau%2C+France-Isabelle%22">Auzanneau, France-Isabelle</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> fauzanne@uoguelph.ca</i>
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  Data: <searchLink fieldCode="JN" term="%22Carbohydrate+Research%22">Carbohydrate Research</searchLink>. Aug2019, Vol. 482, pN.PAG-N.PAG. 1p.
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  Data: <searchLink fieldCode="DE" term="%22Thiourea%22">Thiourea</searchLink><br /><searchLink fieldCode="DE" term="%22Glycosylation%22">Glycosylation</searchLink><br /><searchLink fieldCode="DE" term="%22Epitopes%22">Epitopes</searchLink><br /><searchLink fieldCode="DE" term="%22Fucosylation%22">Fucosylation</searchLink><br /><searchLink fieldCode="DE" term="%22Metals%22">Metals</searchLink><br /><searchLink fieldCode="DE" term="%22Immunoglobulins%22">Immunoglobulins</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: The convergent synthesis of tetra- and penta-saccharide fragments of the TACA dimeric Lex is described. The synthetic strategy relied on the preparation of a protected GlcNTCA-(1,3)-Gal-(1,4)-GlcNAc trisaccharide diol free at O-3 of both glucosamine residues. Key steps in the preparation of this diol involved glycosylation at O-4 of N -acetylglucosamine using activation of a trichloroacetimidate with BF 3 · Et 2 O at 40 °C, removal of the non-reducing end O-3' chloroacetate with thiourea, and glycosylation with a N -trichloroacetamido glucosamine trichloroacetimidate donor. After conversion to the diol acceptor, the trisaccharide was selectively fucosylated at the nonreducing end under NIS/TMSOTf activation, or di-fucosylated under CuBr 2 /Bu 4 NBr activation. The protected tetra- and pentasaccharides were then efficiently deprotected under dissolving metal conditions and the nonreducing end glucosamine residues were N- acetylated during the reaction work up. The deprotected compounds will be used as soluble competitors to characterize the epitopes recognized by anti-polymeric Lex antibodies. Image 1 • Synthesis of tetra- and penta-saccharide fragments of dimeric Lex is described. • A trisaccharide diol free at O-3 of both glucosamine residues was prepared. • The trisaccharide diol was mono-fucosylated under NIS/TMSOTf activation. • The trisaccharide diol was di-fucosylated under CuBr 2 /Bu 4 NBr activation. • Tetra- and pentasaccharides were deprotected under dissolving metal conditions. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
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  Data: <i>Copyright of Carbohydrate Research is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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      – Type: doi
        Value: 10.1016/j.carres.2019.06.009
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      – Code: eng
        Text: English
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      – SubjectFull: Thiourea
        Type: general
      – SubjectFull: Glycosylation
        Type: general
      – SubjectFull: Epitopes
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      – SubjectFull: Fucosylation
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      – SubjectFull: Metals
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      – SubjectFull: Immunoglobulins
        Type: general
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      – TitleFull: Convergent synthesis of tetra- and penta-saccharide fragments of dimeric Lewis X.
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            NameFull: Forman, Adam
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            NameFull: Hendel, Jenifer
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            NameFull: Auzanneau, France-Isabelle
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            – D: 01
              M: 08
              Text: Aug2019
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              Y: 2019
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              Value: 482
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