Chemoenzymatic synthesis of the sialyl Lewis X glycan and its derivatives

Amo, David Soriano del; Wang, Wei; Besanceney, Christen; Zheng, Tianqing; He, Yizheng; Gerwe, Brian A.; Seidel, R.D.; Wu, Peng

doi:10.1016/j.carres.2010.03.032

Cited by 18 publications

(15 citation statements)

References 28 publications

(25 reference statements)

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“…CeFUT6 has a known Lewis‐X fucosylation activity which was employed in this study to yield O8 from O7 in 73 % yield . HP‐FucT has a broad substrate and donor specificity including the C‐6 azido‐fucose surrogate (FucZ) . Introducing an azide function as a biorthogonal handle in the molecule opened the possibility of generating glycomimetics by copper‐catalyzed cycloaddition with alkynes to afford a library of novel glycomimetics with potentially improved affinity towards CLRs …”

Section: Resultsmentioning

confidence: 99%

Chemo‐Enzymatic Synthesis of S. mansoni O‐Glycans and Their Evaluation as Ligands for C‐Type Lectin Receptors MGL, DC‐SIGN, and DC‐SIGNR

Pham

Hernandez

Cioce

et al. 2020

Chemistry A European J

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Due to their interactions with C‐type lectin receptors (CLRs), glycans from the helminth Schistosoma mansoni represent promising leads for treatment of autoimmune diseases, allergies or cancer. We chemo‐enzymatically synthesized nine O‐glycans based on the two predominant O‐glycan cores observed in the infectious stages of schistosomiasis, the mucin core 2 and the S. mansoni core. The O‐glycans were fucosylated next to a selection of N‐glycans directly on a microarray slide using a recombinant fucosyltransferase and GDP‐fucose or GDP‐6‐azidofucose as donor. Binding assays with fluorescently labelled human CLRs DC‐SIGN, DC‐SIGNR and MGL revealed the novel O‐glycan O8 as the best ligand for MGL from our panel. Significant binding to DC‐SIGN was also found for azido‐fucosylated glycans. Contrasting binding specificities were observed between the monovalent carbohydrate recognition domain (CRD) and the tetravalent extracellular domain (ECD) of DC‐SIGNR.

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Section: Resultsmentioning

confidence: 99%

Chemo‐Enzymatic Synthesis of S. mansoni O‐Glycans and Their Evaluation as Ligands for C‐Type Lectin Receptors MGL, DC‐SIGN, and DC‐SIGNR

Pham

Hernandez

Cioce

et al. 2020

Chemistry A European J

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“…With this convergent synthesis strategy in place, a chemo-enzymatic approach to the synthesis of D1 and D2/D3 arm donors was explored to allow a rapid assembly of diverse N -glycans 55,56 . To this end, various glycosyl transferases were used, including β-1,4-galactosyltransferases 51,57 , α-2,3/2,6-sialyltransferases 52,53 and α-1,3/1,2-fucosyltransferases 49,51,58 , for the preparation of linear and branched modules by enzymatic extension of chemically synthesized acceptors 16–20 (Fig. 3 and Supplementary Scheme 22).…”

Section: Resultsmentioning

confidence: 99%

Modular synthesis of N-glycans and arrays for the hetero-ligand binding analysis of HIV antibodies

et al. 2016

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A new class of broadly neutralizing antibodies (bNAbs) from HIV donors has been reported to target the glycans on gp120, thus renewing hope of developing carbohydrate-based HIV vaccines. However, the version of gp120 used in previous studies was not from human T cells and so the glycosylation pattern could be somewhat different to that found in the native system. Moreover, some antibodies recognized two different glycans simultaneously and this cannot be detected with the commonly used glycan microarrays on glass slides. Here, we have developed a glycan microarray on an aluminium oxide-coated glass slide containing a diverse set of glycans, including homo- and mixed N-glycans (high-mannose, hybrid and complex types) that were prepared by modular chemo-enzymatic methods to detect the presence of hetero-glycan binding behaviours. This new approach allows rapid screening and identification of optimal glycans recognized by neutralizing antibodies, and could speed up the development of HIV-1 vaccines targeting cell surface glycans.

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“…1A and B). Due to its high Km (1.3 mM) and high kcat (442 min -1 ) (Soriano del Amo et al, 2010;Zheng et al, 2011), the membrane anchored FT is ideal to enable proximity-dependent labeling of prey cells that interact with bait cells harboring the enzyme (Fig. 1A).…”

Section: Install H Pylori α1-3-fucosyltransferase (Ft) Onto the Cellmentioning

confidence: 99%

Detecting Tumor Specific Antigen-Reactive T cells from Tumor Infiltrating Lymphocytes via Interaction Dependent Fucosyl-biotinylation

Liu

Chen

et al. 2020

Preprint

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HighlightsInteraction dependent fucosylation enables the detection and isolation of bona fide intratumoral tumor specific antigen-reactive T cells Tumor specific antigen-reactive CD8 + T cells possess capabilities to be expanded and adoptively transferred for tumor control Tumor specific antigen-reactive CD8 + T cells feature oligoclonal expansion and upregulate genes for the steroid biosynthesis and metabolic process Intratumoral bystander CD8 + T cells can be separated into two groups based on PD-1 expression that feature distinct gene modules SummaryRe-activation and clonal expansion of tumor specific antigen (TSA)-reactive T cells are critical to the success of checkpoint blockade and adoptive transfer of tumor-infiltrating lymphocyte (TIL) based therapies. There are no reliable markers to specifically identify the repertoire of TSA-reactive T cells due to their heterogeneous composition. Here we introduce FucoID as a general platform to detect endogenous antigen-specific T cells and study their biology. Through this interaction dependent labeling approach, TSA-reactive T cells can be detected and separated from bystander T cells in primary tumor digests based on their cell-surface enzymatic fucosylbiotinylation. Compared to bystander TILs, TSA-reactive TILs possess a distinct TCR repertoire and unique gene features. Though exhibiting a dysfunctional phenotype, this subset of TILs possesses substantial capabilities of proliferation and tumor specific killing. FucoID features genetic manipulation-free procedures and a quick turnover cycle, and therefore should have the potential of accelerating the pace of personalized cancer treatment.

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Chemoenzymatic synthesis of the sialyl Lewis X glycan and its derivatives

Cited by 18 publications

References 28 publications

Chemo‐Enzymatic Synthesis of S. mansoni O‐Glycans and Their Evaluation as Ligands for C‐Type Lectin Receptors MGL, DC‐SIGN, and DC‐SIGNR

Chemo‐Enzymatic Synthesis of S. mansoni O‐Glycans and Their Evaluation as Ligands for C‐Type Lectin Receptors MGL, DC‐SIGN, and DC‐SIGNR

Modular synthesis of N-glycans and arrays for the hetero-ligand binding analysis of HIV antibodies

Detecting Tumor Specific Antigen-Reactive T cells from Tumor Infiltrating Lymphocytes via Interaction Dependent Fucosyl-biotinylation

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