Polylactosamines, there’s more than meets the “Ii”: a review of the I system

Cooling, Laura

doi:10.21307/immunohematology-2019-213

Cited by 18 publications

(7 citation statements)

References 137 publications

(308 reference statements)

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“…The position of I-branch regioselectivity imposed by Nmodified glucosamine was confirmed by a combination of 1…”

Section: Selective I-branch Activity Imposed By N-modified Glucosamin...mentioning

confidence: 86%

“…The latter can be accomplished by printing synthetic glycans as a microarray for rapid structure-binding studies. [23] Experimental Section Material and methods: 1 13 C NMR signal assignment was extracted from 2D HSQC spectra. Mass spectra are recorded by ESI on a Bruker micrOTOF-QII system as m/z.…”

Section: Discussionmentioning

confidence: 99%

“…This glycan structure is based on a lactose core that is present on HMOs and polyglycosylceramides, which are glycan classes that are often modified by I-branches. [1,16] Benzyl lactoside 1 was used as the starting material because its anomeric center is locked in one anomeric configuration and furthermore the benzyl moiety increases sensitivity for MS and UV absorption based detection thereby facilitating identification and purification. Benzyl glycoside 1, which was generated by a four-step procedure involving Koenigs-Knorr glycosylation of lactose with benzyl alcohol, was enzymatically extended to lacto-neo-N-tetraose 2 and then to lacto-neo-N-hexaose 3 by the alternating action of beta-1,3-Nacetylglucosaminyltransferase 2 (B3GNT2) and beta-1,4-galactosyltransferase 1 (B4GalT1).…”

Section: Examining the Regioselectivity Of Gcnt2mentioning

confidence: 99%

“…The topology of polyLacNAc chains also forms the basis of the Ii blood group system classification. [1] The i antigen is a linear β1,3-linked polyLacNAc chain that enzymatically can be converted into an I antigen by the I-branching enzyme beta-1,6-N-acetylglucosaminyltransferase 2 (GCNT2), which introduces a β-linked GlcNAc moiety at the 6-position of internal galactosides of i antigens (Figure 1A). This branching point can be extended by glycosyltransferases in a similar manner as the main glycan chain to form I-branched multi-antennary glycans.…”

Section: Introductionmentioning

confidence: 99%

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Chemo‐Enzymatic Synthesis of Isomeric I‐branched Polylactosamines Using Traceless Blocking Groups

Vos,

Wu,

van der Woude

et al. 2023

Chemistry A European J

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Poly‐N‐acetyl lactosamines (polyLacNAc) are common structural motifs of N‐ and O‐linked glycan, glycosphingolipids and human milk oligosaccharides. They can be branched by the addition of β1,6‐linked N‐acetyl‐glucosamine (GlcNAc) moieties to internal galactoside (Gal) residues by the I‐branching enzyme beta‐1,6‐N‐acetylglucosaminyltransferase 2 (GCNT2). I‐branching has been implicated in many biological processes and is also associated with various diseases such as cancer progression. Currently, there is a lack of methods that can install, in a regioselective manner, I‐branches and allows the preparation of isomeric poly‐LacNAc derivatives. Here, we described a chemo‐enzymatic strategy that addresses this deficiency and is based on the enzymatic assembly of an oligo‐LacNAc chain that at specific positions is modified by a GlcNTFA moiety. Replacement of the trifluoroacetyl (TFA) moiety by tert‐butyloxycarbonyl (Boc) gives compounds in which the galactoside at the proximal site is blocked from modification by GCNT2. After elaboration of the antennae, the Boc group can be removed, and the resulting amine acetylated to give natural I‐branched structures. It is also shown that fucosides can function as a traceless blocking group that can provide complementary I‐branched structures from a single precursor. The methodology made it possible to synthesize a library of polyLacNAc chains having various topologies.

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“…The position of I-branch regioselectivity imposed by Nmodified glucosamine was confirmed by a combination of 1…”

Section: Selective I-branch Activity Imposed By N-modified Glucosamin...mentioning

confidence: 86%

Section: Discussionmentioning

confidence: 99%

Section: Examining the Regioselectivity Of Gcnt2mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Chemo‐Enzymatic Synthesis of Isomeric I‐branched Polylactosamines Using Traceless Blocking Groups

Vos,

Wu,

van der Woude

et al. 2023

Chemistry A European J

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“…Therefore, the antibody titer can increase under such infectious disease conditions, which may lead to hemolysis. In addition, cross-reactivity and molecular mimicry may cause a rise in cold agglutinins after infection ( 14 ). As such, SARS-CoV-2 may have similarity to Mycoplasma pneumoniae , making this one possible explanation for the existence of COVID-19-related CAS.…”

Section: Discussionmentioning

confidence: 99%

Severe Anemia Due to Cold Agglutinin Syndrome in a COVID-19 Patient with IgM Monoclonal Gammopathy of Undetermined Significance Successfully Treated with Corticosteroids

et al. 2022

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Secondary cold agglutinin syndrome (CAS) is autoimmune hemolytic anemia secondary to infections and lymphoid disorder. We here report the first Asian case of CAS secondary to novel coronavirus disease 2019 (COVID-19). A 72-year-old Japanese woman presented with a 2-week history of dyspnea and cough, and laboratory data revealed severe hemolytic anemia with a hemoglobin level of 4.7 g/dL. She was diagnosed with COVID-19, CAS, and monoclonal gammopathy of undetermined significance (MGUS). The anemia responded to corticosteroids administered for COVID-19 and required maintenance therapy. Although corticosteroids are not a standard therapy for CAS, they might be effective for CAS secondary to COVID-19 complicated with MGUS.

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I and i Antigens, and Cold Agglutination

Daniels

2013

Human Blood Groups

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Polylactosamines, there’s more than meets the “Ii”: a review of the I system

Cited by 18 publications

References 137 publications

Chemo‐Enzymatic Synthesis of Isomeric I‐branched Polylactosamines Using Traceless Blocking Groups

Chemo‐Enzymatic Synthesis of Isomeric I‐branched Polylactosamines Using Traceless Blocking Groups

Severe Anemia Due to Cold Agglutinin Syndrome in a COVID-19 Patient with IgM Monoclonal Gammopathy of Undetermined Significance Successfully Treated with Corticosteroids

I and i Antigens, and Cold Agglutination

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