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3 article(s) from Delbianco, Martina

Linker, loading, and reaction scale influence automated glycan assembly

Marlene C. S. Dal Colle,
Manuel G. Ricardo,
Nives Hribernik,
José Danglad-Flores,
Peter H. Seeberger and
Martina Delbianco

Beilstein J. Org. Chem. 2023, 19, 1015–1020, doi:10.3762/bjoc.19.77

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Figure 1: Schematic representation of the AGA process (A). Variables that can affect the AGA outcome investig...

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Figure 2: AGA of model glycan sequences analyzed in this study: α-1,6-linked dimannosides 1, 2 (A), branched ...

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Figure 3: Representative HPLC traces for the crude compounds 1 (A), 3 (B), and 5a (C) after cleavage from the...

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Letter

Published 06 Jul 2023

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Progress and challenges in the synthesis of sequence controlled polysaccharides

Giulio Fittolani,
Theodore Tyrikos-Ergas,
Denisa Vargová,
Manishkumar A. Chaube and
Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

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Figure 1: Overview of the methods available for the synthesis of polysaccharides. For each method, advantages...

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Figure 2: Overview of the classes of polysaccharides discussed in this review. Each section deals with polysa...

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Scheme 1: Enzymatic and chemical polymerization approaches provide cellulose oligomers with a non-uniform dis...

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Scheme 2: AGA of a collection of cellulose analogues obtained using BBs 6–9. Specifically placed modification...

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Figure 3: Chemical structure of the different branches G, X, L, F commonly found in XGs. Names are given foll...

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Scheme 3: AGA of XG analogues with defined side chains. The AGA cycle includes coupling (TMSOTf), Fmoc deprot...

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Figure 4: Synthetic strategies and issues associated to the formation of the β(1–3) linkage.

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Scheme 4: Convergent synthesis of β(1–3)-glucans using a regioselective glycosylation strategy.

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Scheme 5: DMF-mediated 1,2-cis glycosylation. A) General mechanism and B) examples of α-glucans prepared usin...

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Scheme 6: Synergistic glycosylation strategy employing a nucleophilic modulation strategy (TMSI and Ph₃PO) in...

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Scheme 7: Different approaches to produce xylans. A) Polymerization techniques including ROP, and B) enzymati...

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Scheme 8: A) Synthesis of arabinofuranosyl-decorated xylan oligosaccharides using AGA. Representative compoun...

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Scheme 9: Chemoenzymatic synthesis of COS utilizing a lysozyme-catalyzed transglycosylation reaction followed...

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Scheme 10: Synthesis of COS using an orthogonal glycosylation strategy based on the use of two different LGs.

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Scheme 11: Orthogonal N-PGs permitted the synthesis of COS with different PA.

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Scheme 12: AGA of well-defined COS with different PA using two orthogonally protected BBs. The AGA cycle inclu...

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Scheme 13: A) AGA of β(1–6)-N-acetylglucosamine hexasaccharide and dodecasaccharide. AGA includes cycles of co...

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Figure 5: ‘Double-faced’ chemistry exemplified for ᴅ-Man and ʟ-Rha. Constructing β-Man linkages is considerab...

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Figure 6: Implementation of a capping step after each glycosylation cycle for the AGA of a 50mer oligomannosi...

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Scheme 14: AGA enabled the synthesis of a linear α(1–6)-mannoside 100mer 93 within 188 h and with an average s...

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Scheme 15: The 151mer branched polymannoside was synthesized by a [30 + 30 + 30 + 30 + 31] fragment coupling. ...

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Figure 7: PG stereocontrol strategy to obtain β-mannosides. A) The mechanism of the β-mannosylation reaction ...

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Scheme 16: A) Mechanism of 1,2-cis stereoselective glycosylation using ManA donors. Once the ManA donor is act...

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Figure 8: A) The preferred ⁴H₃ conformation of the gulosyl oxocarbenium ion favors the attack of the alcohol ...

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Scheme 17: AGA of type I rhamnans up to 16mer using disaccharide BB 115 and CNPiv PG. The AGA cycle includes c...

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Figure 9: Key BBs for the synthesis of the O-antigen of Bacteroides vulgatus up to a 128mer (A) and the CPS o...

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Figure 10: Examples of type I and type II galactans synthesized to date.

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Figure 11: A) The DTBS PG stabilizes the ³H₄ conformation of the Gal oxocarbenium ion favoring the attack of t...

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Figure 12: Homogalacturonan oligosaccharides synthesized to date. Access to different patterns of methyl-ester...

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Figure 13: GlfT2 from Mycobacterium tuberculosis catalyzes the sequential addition of UPD-Galf donor to a grow...

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Figure 14: The poor reactivity of acceptor 137 hindered a stepwise synthesis of the linear galactan backbone a...

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Scheme 18: AGA of a linear β(1–5) and β(1–6)-linked galactan 20mer. The AGA cycle includes coupling (NIS/TfOH)...

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Figure 15: The 92mer arabinogalactan was synthesized using a [31 + 31 + 30] fragment coupling between a 31mer ...

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Scheme 19: Synthesis of the branched arabinofuranose fragment using a six component one-pot synthesis. i) TTBP...

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Figure 16: A) Chemical structure and SNFG of the representative disaccharide units forming the GAG backbones, ...

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Figure 17: Synthetic challenges associated to the H/HS synthesis.

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Scheme 20: Degradation of natural heparin and heparosan generated valuable disaccharides 150 and 151 that can ...

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Scheme 21: A) The one-step conversion of cyanohydrin 156 to ʟ-iduronamide 157 represent the key step for the s...

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Scheme 22: A) Chemoenzymatic synthesis of heparin structures, using different types of UDP activated natural a...

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Scheme 23: Synthesis of the longest synthetic CS chain 181 (24mer) using donor 179 and acceptor 180 in an iter...

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Scheme 24: AGA of a collection of HA with different lengths. The AGA cycle includes coupling (TfOH) and Lev de...

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Review

Published 05 Aug 2021

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Automated glycan assembly of arabinomannan oligosaccharides from Mycobacterium tuberculosis

Alonso Pardo-Vargas,
Priya Bharate,
Martina Delbianco and
Peter H. Seeberger

Beilstein J. Org. Chem. 2019, 15, 2936–2940, doi:10.3762/bjoc.15.288

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Scheme 1: Schematic representation of AGA for oligomannosides and oligoarabinomannosides using building block...

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Figure 1: HPLC chromatograms of crude dodecamer 9. a) Results obtained with AGA procedure A. b) Results obtai...

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Figure 2: Schematic representation of LAM and AM oligomers obtained using AGA.

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Full Research Paper

Published 06 Dec 2019

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