Highly convergent synthesis of a β-mannuronic acid alginate hexadecasaccharide

Pan, Dingyi; Zhang, Liangliang; Hua, Qingting; Yang, You

doi:10.1039/c9ob01254k

Cited by 12 publications

(9 citation statements)

References 38 publications

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“…A solution-phase approach allowed to reduce the amount of required donor (1–2 equiv compared to 9 equiv) and to couple big fragments (i.e., [4 + 4] and [8 + 8] glycosylations) without a significant loss in β-stereoselectivity. A β(1–4)-ManA 16mer was prepared using this highly convergent and iterative approach [ 303 ].…”

Section: Reviewmentioning

confidence: 99%

Progress and challenges in the synthesis of sequence controlled polysaccharides

Fittolani¹,

Tyrikos‐Ergas²,

Vargová³

et al. 2021

Beilstein J. Org. Chem.

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The sequence, length and substitution of a polysaccharide influence its physical and biological properties. Thus, sequence controlled polysaccharides are important targets to establish structure–properties correlations. Polymerization techniques and enzymatic methods have been optimized to obtain samples with well-defined substitution patterns and narrow molecular weight distribution. Chemical synthesis has granted access to polysaccharides with full control over the length. Here, we review the progress towards the synthesis of well-defined polysaccharides. For each class of polysaccharides, we discuss the available synthetic approaches and their current limitations.

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Section: Reviewmentioning

confidence: 99%

Progress and challenges in the synthesis of sequence controlled polysaccharides

Fittolani¹,

Tyrikos‐Ergas²,

Vargová³

et al. 2021

Beilstein J. Org. Chem.

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“…The natural abundance, biomedical importance of mannuronates, improved understanding of reaction mechanisms, and advancements of chemical methods have stimulated a notable interest in synthesizing many alginates and alginate‐like glycan sequences in recent years [50,71–82] . Noteworthy is the convergent solution‐phase synthesis of β ‐ManA alginate hexadecasaccharide oligomer.…”

Section: Mannuronic Acid (Mana) Glycosidesmentioning

confidence: 99%

“…Noteworthy is the convergent solution‐phase synthesis of β ‐ManA alginate hexadecasaccharide oligomer. It was obtained following the [8+8] coupling of octamannuronate N ‐phenyl trifluoroacetimidate donor and octamannuronate acceptor [82] . The developed methodology has even enabled the automated synthesis to obtain alginate oligomers [50] .…”

Section: Mannuronic Acid (Mana) Glycosidesmentioning

confidence: 99%

“…[70][71][72] The natural abundance, biomedical importance of mannuronates, improved understanding of reaction mechanisms, and advancements of chemical methods have stimulated a notable interest in synthesizing many alginates and alginatelike glycan sequences in recent years. [50,[71][72][73][74][75][76][77][78][79][80][81][82] Noteworthy is the convergent solution-phase synthesis of β-ManA alginate hexadecasaccharide oligomer. It was obtained following the [8 + 8] coupling of octamannuronate N-phenyl trifluoroacetimidate donor and octamannuronate acceptor.…”

Section: Mannuronic Acid (Mana) Glycosidesmentioning

confidence: 99%

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Recent Advances in Stereocontrolled Mannosylation: Focus on Glycans Comprising Acidic and/or Amino Sugars

Alex

Demchenko

2021

The Chemical Record

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The main focus of this review is to describe accomplishments made in the stereoselective synthesis of β‐linked mannosides functionalized with carboxyls or amines/amides. These ManNAc, ManA and ManNAcA residues found in many glycoconjugates, bacterial polysaccharides, and alginates have consistently captured interest of the glycoscience community both due to synthetic challenge and therapeutic potential.

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“…To this end, synthetic chemistry strategies (both solution and solid phase) have demonstrated exciting capabilities for access to native alginate oligosaccharides in recent years [6][7][8][9][10]. As part of a program to access non-native alginate oligosaccharide sequences, we targeted a synthetic approach to provide structurally defined building blocks containing bioisosteres of ᴅ-mannuronic acid.…”

Section: Introductionmentioning

confidence: 99%

Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate

Dimitriou¹,

Miller²

2021

Beilstein J. Org. Chem.

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Alginate is a biocompatible and industrially relevant polysaccharide that derives many of its important properties from the charged carboxylate groups within its polyuronic acid backbone. The design and inclusion of isosteric replacements for these carboxylates would underpin provision of new oligo-/polysaccharide materials with alternate physicochemical properties. Presented herein is our synthesis of mannuronic acid building blocks, appropriately modified at the carboxylate C6 position with a bioisosteric tetrazole. Thioglycosides containing a protected C6-tetrazole are accessed from a C6-nitrile, through dipolar cycloaddition using NaN3 with n-Bu2SnO. We also demonstrate access to orthogonally C4-protected donors, suitable for iterative oligosaccharide synthesis. The development of these building blocks is showcased to access anomeric 3-aminopropyl- and 1-phosphate free sugars containing this non-native motif.

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Highly convergent synthesis of a β-mannuronic acid alginate hexadecasaccharide

Abstract: Highly convergent synthesis of a β-mannuronic acid alginate hexadecasaccharide representing the longest synthetic polymannuronic acid so far is achieved.

Cited by 12 publications

References 38 publications

Progress and challenges in the synthesis of sequence controlled polysaccharides

Progress and challenges in the synthesis of sequence controlled polysaccharides

Recent Advances in Stereocontrolled Mannosylation: Focus on Glycans Comprising Acidic and/or Amino Sugars

Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate

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