Improved synthesis of O-linked, and first synthesis of S- linked, carbohydrate functionalised N-carboxyanhydrides (glycoNCAs)

Gibson, Matthew I.; Hunt, Gregory; Cameron, Neil R.

doi:10.1039/b707563d

Cited by 35 publications

(34 citation statements)

References 24 publications

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“…cyclization of the Boc amino acids with triphosgene failed to yield the NCAs in a single step, which has also been observed with other bulky substituents. [18] Therefore, the Boc group was removed with HCl and the NCAs 9 and 10 obtained by reaction with triphosgene in 38% and 44% yield, respectively. Rigorous purification, by basic aqueous extraction, yielded the NCAs without detectable amino acid impurities.…”

Section: Evaluation Of Nonspecific Protein Adsorptionmentioning

confidence: 99%

Nonfouling Polypeptide Brushes via Surface‐initiated Polymerization of N^ε‐oligo(ethylene glycol)succinate‐L‐lysine N‐carboxyanhydride

Wang

Gibson

Barbey

et al. 2009

Macromol. Rapid Commun.

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This contribution describes the preparation of nonfouling polypeptide brushes via surface-initiated ring-opening polymerization of oligo(ethylene glycol) modified L-lysine N-carboxyanhydrides. Circular dichroism experiments indicated that these surface-anchored polypeptide chains assume an α-helical conformation, which does not change between pH 4 and 9. Furthermore, nonspecific adsorption of fluorescent labeled bovine serum albumin and fibrinogen on glass slides modified with these brushes was greatly reduced compared to unmodified glass substrates.

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Section: Evaluation Of Nonspecific Protein Adsorptionmentioning

confidence: 99%

Nonfouling Polypeptide Brushes via Surface‐initiated Polymerization of N^ε‐oligo(ethylene glycol)succinate‐L‐lysine N‐carboxyanhydride

Wang

Gibson

Barbey

et al. 2009

Macromol. Rapid Commun.

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“…[8] Another strategy investigated by Nishimura and coworkers [9] and Takasu et al [10] was the glycopolypeptides with diverse glycopendants and well-defined secondary structures synthesized by the condensation polymerization of glycosylated tripeptides monomers. Block copolymerization of glycopolymers/polysaccharides with polypeptides, reported by Dong et al [11] and Lecommandoux and coworkers, [12] are attractive new ways to glycopeptide mimics which is able to self-assemble into glyconanoparticles in aqueous medium due to their amphiphilic properties.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Glycopolypeptides by Combination of Ring‐Opening Polymerization of an Alkyne‐Substituted N‐carboxyanhydride and Click “Glycosylation”

Xiao¹,

Zhao²,

He³

et al. 2010

Macromol. Rapid Commun.

147

156

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Synthetic glycopolypeptides have attracted much interest for application in biomedical field as they are structural mimics to the natural glycopeptides or glycoproteins. However, the synthesis methods toward glycopolypeptides are still few or less efficient. Herein, we present a facile route to preparation of glycopolypeptides with highly effective "glycosylation" by click postpolymerization modification. First, an alkyne-substituted N-carboxyanhydride (NCA) monomer was synthesized and subsequently polymerized to afford the polypeptide with "clickable" alkyne pendants. The alkyne-functionalized polypeptide was then "glycosylated" by click reaction of different sugar azides to the alkyne pendants with high efficiency. All the obtained glycopolypeptides were soluble and preferred α-helix conformation in water. Primary studies on the obtained glycopolypeptides binding with Con A lectin were assessed by turbidimetric assay. The more quantitive studies of the interactions between lectin proteins and the synthetic glycopolypeptides, and the application of these materials as the multivalent ligands are in progress.

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“…The main strategies for the synthesis of glycopolypeptides are the polymerization of glycosylated monomers and the post‐polymerization glycosylation. Polymerization of glycosylated N ‐carboxyanhydrides (NCA) allows 100% glycosylation of the polypeptide, but the synthesis is complex and for each sugar a new NCA‐monomer has to be prepared . A higher variability in the choice of the sugar can be achieved by post‐polymerization glycosylation.…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis of pH‐responsive glycopolypeptides with adjustable sugar density

Mildner

Menzel

2013

J. Polym. Sci. Part A: Polym. Chem.

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Well‐defined pH‐responsive glycopolypeptides were prepared by polymer‐analogous aqueous amide coupling of d‐glucosamine to poly(α,l‐glutamic acid) (PGA) using the coupling agent 4‐(4,6‐dimethoxy‐1,3,5‐triazin‐2‐yl)‐4‐methylmorpholinium chloride (DMT‐MM) without any organic solvents, additives, or buffers. Degrees of substitution (DS) up to 80% can be achieved, and the DS is adjustable by the molar ratio of DMT‐MM to PGA repeating units. Successful glycosylation of both low MW and high MW PGA was confirmed by 1H NMR and FTIR spectroscopy as well as by an enhanced solubility at low pH. CD spectroscopy revealed that glycosylated PGAs with a DS up to 0.63 are able to undergo a pH‐responsive and reversible helix‐coil transition. However, for polymers with higher DS no transition occurs. A comparison with PGAs functionalized with monoethanolamine showed that the low helicity at high DS is not a steric effect due to the bulky sugar moieties, but a solvation effect. Preliminary turbidimetric tests with the lectin Concanavalin A indicate a biological activity of these glycosylated polypeptides. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3925–3931

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Improved synthesis of O-linked, and first synthesis of S- linked, carbohydrate functionalised N-carboxyanhydrides (glycoNCAs)

Abstract: An improved method for the synthesis of glycosylated N-carboxyanhydrides, which are monomers for glycopeptide synthesis, is presented.

Cited by 35 publications

References 24 publications

Nonfouling Polypeptide Brushes via Surface‐initiated Polymerization of N^ε‐oligo(ethylene glycol)succinate‐L‐lysine N‐carboxyanhydride

Nonfouling Polypeptide Brushes via Surface‐initiated Polymerization of N^ε‐oligo(ethylene glycol)succinate‐L‐lysine N‐carboxyanhydride

Facile Synthesis of Glycopolypeptides by Combination of Ring‐Opening Polymerization of an Alkyne‐Substituted N‐carboxyanhydride and Click “Glycosylation”

Facile synthesis of pH‐responsive glycopolypeptides with adjustable sugar density

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Improved synthesis of O-linked, and first synthesis of S- linked, carbohydrate functionalised N-carboxyanhydrides (glycoNCAs)

Abstract: An improved method for the synthesis of glycosylated N-carboxyanhydrides, which are monomers for glycopeptide synthesis, is presented.

Cited by 35 publications

References 24 publications

Nonfouling Polypeptide Brushes via Surface‐initiated Polymerization of Nε‐oligo(ethylene glycol)succinate‐L‐lysine N‐carboxyanhydride

Nonfouling Polypeptide Brushes via Surface‐initiated Polymerization of Nε‐oligo(ethylene glycol)succinate‐L‐lysine N‐carboxyanhydride

Facile Synthesis of Glycopolypeptides by Combination of Ring‐Opening Polymerization of an Alkyne‐Substituted N‐carboxyanhydride and Click “Glycosylation”

Facile synthesis of pH‐responsive glycopolypeptides with adjustable sugar density

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Nonfouling Polypeptide Brushes via Surface‐initiated Polymerization of N^ε‐oligo(ethylene glycol)succinate‐L‐lysine N‐carboxyanhydride

Nonfouling Polypeptide Brushes via Surface‐initiated Polymerization of N^ε‐oligo(ethylene glycol)succinate‐L‐lysine N‐carboxyanhydride