Convenient Routes to Efficiently N-PEGylated Peptides

Stutz, Christian; Meszyńska, Anna; Lutz, Jean‐François; Börner, Hans G.

doi:10.1021/mz400260e

Cited by 12 publications

(11 citation statements)

References 36 publications

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“…The reaction of polymer 4 with a simpler azide, (2S)-2-azido-3-methylbutanoic acid, was also attempted under the same conditions. Following purification by SEC using Sephadex LH-20, the product was analysed by 13 C NMR, but no signal characteristic of the triazole ring could be observed in its spectrum. This absence of conversion is unexpected as the azide-alkyne cyclo-addition has been successfully used in a number of challenging applications, including polymer chemistry.…”

Section: Peg Derivatives For Multiple Conjugation Of Peptides By Azidmentioning

confidence: 99%

“…Synthesis of poly(glycidyl amine) (13). This was conjugated to a peptide amide with a free carboxylic acid (Ac-GWYRGRLE) 14 ( Figure 4).…”

Section: Synthesis Of Poly(glycidyl Amine)mentioning

confidence: 99%

“…Multiplicities are denoted by s (singlet), d (doublet), t (triplet), q (quartet), dd (double of doublets), m (multiplets), br (broad), bb (polymer backbone). 1 H, 13 C data are included for each compound, where appropriate. MALDI-TOF MS for relevant samples were obtained on an AB Sciex 4800 MALDI-TOF/TOF (AB Sciex UK Ltd., Cheshire, UK), using α-cyano-4-hydroxycinnamic acid (CHCA) as a matrix.…”

Section: General Experimental Proceduresmentioning

confidence: 99%

“…NMR analysis, based on the tert-butyl group signal determines the polymer to have an average length of 12 units. Poly(glycidyl amine) (13). Amine deprotection was carried out by dissolving the polymer (400 mg, 2.3 mmol) in dichloromethane (2 mL) and trifluoroacetic acid (2 mL).…”

Section: Polymer Synthesismentioning

confidence: 99%

“…Polyethylene glycol (PEG) in particular has been successfully exploited to improve the solubility, stability and prevent the toxicity of its cargoes, notably peptides [12,13] and proteins [10]. First and second generation PEGs, based on a linear backbone, are inherently characterised by a low loading capacity.…”

Section: Introductionmentioning

confidence: 99%

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Poly(Ethylene Glycol)-Based Backbones with High Peptide Loading Capacities

et al. 2014

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Polymer-peptide conjugates are a promising class of compounds, where polymers can be used to overcome some of the limitations associated with peptides intended for therapeutic and/or diagnostic applications. Linear polymers such as poly(ethylene glycol) can be conjugated through terminal moieties and have therefore limited loading capacities. In this research, functionalised linear poly(ethylene glycol)s are utilised for peptide conjugation, to increase their potential loading capacities. These poly(ethylene glycol) derivatives are conjugated to peptide sequences containing representative side-chain functionalised amino acids, using different conjugation chemistries, including copper-catalysed azide-alkyne cycloaddition, amide coupling and thiol-ene reactions. Conjugation of a sequence containing the RGD motif to poly(allyl glycidyl ether) by the thiol-ene reaction, provided a conjugate which could be used in platelet adhesion studies.

show abstract

Section: Peg Derivatives For Multiple Conjugation Of Peptides By Azidmentioning

confidence: 99%

“…Synthesis of poly(glycidyl amine) (13). This was conjugated to a peptide amide with a free carboxylic acid (Ac-GWYRGRLE) 14 ( Figure 4).…”

Section: Synthesis Of Poly(glycidyl Amine)mentioning

confidence: 99%

Section: General Experimental Proceduresmentioning

confidence: 99%

Section: Polymer Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Poly(Ethylene Glycol)-Based Backbones with High Peptide Loading Capacities

et al. 2014

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Peptide Synthesis and Beyond the Use of Sequence‐Defined Segments for Materials Science

Brummelhuis

Wilke

Börner

2017

Sequence‐Controlled Polymers

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Preparation of Information‐Containing Macromolecules by Ligation of Dyad‐Encoded Oligomers

Trinh

Oswald

Chan‐Seng

et al. 2015

Chemistry A European J

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A simplified strategy for preparing non-natural information-containing polymers is reported. The concept relies on the successive ligation of oligomers that contain minimal sequence motifs. It was applied here to the synthesis of digitally-encoded poly(triazole amide)s, in which propyl and 2-methyl propyl motifs are used to code 0 and 1, respectively. A library of four oligo(triazole amide)s containing the information dyads 00, 01, 10, and 11 was prepared. These oligomers contain two reactive functions, that is, an alkyne and a carboxylic acid. Thus, they can be linked to another with the help of a reactive spacer containing azide and amine functions. Using two successive chemoselective steps, that is, azide-alkyne Huisgen cycloaddition and carboxylic acid-amine coupling, monodisperse polymers can be obtained. In particular, the library of dyads permits the implementation of any desired sequence using a small number of steps. As a proof-of-concept, the synthesis of molecular bytes 00000000 and 00000110 is described.

show abstract

Convenient Routes to Efficiently N-PEGylated Peptides

Cited by 12 publications

References 36 publications

Poly(Ethylene Glycol)-Based Backbones with High Peptide Loading Capacities

Poly(Ethylene Glycol)-Based Backbones with High Peptide Loading Capacities

Peptide Synthesis and Beyond the Use of Sequence‐Defined Segments for Materials Science

Preparation of Information‐Containing Macromolecules by Ligation of Dyad‐Encoded Oligomers

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