Synthesis of glycopolypeptides by the ring opening polymerization of O-glycosylated-α-amino acid N-carboxyanhydride (NCA)

Pati, Debasis; Shaikh, Ashif Y.; Hotha, Srinivas; Gupta, Sayam Sen

doi:10.1039/c0py00412j

Cited by 54 publications

(49 citation statements)

References 26 publications

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“…The Gupta group prepared the water soluble lysine-based O-glycopolypeptides via ROP of NCAs. 65 They investigated the selective binding of the poly(a-manno-O-lys) with the lectin ConA using precipitation, hemagglutination assays, and isothermal titration calorimetry (ITC). 66 To investigate the secondary structure effects on the binding affinity, they also prepared racemic D,L-glycopolypeptides, and found that there is no significant difference in binding affinity between helical L-glycopolypeptide and racglycopolypeptide with random coil conformation.…”

Section: Biomolecule Responsive Polypeptidesmentioning

confidence: 99%

Stimuli‐responsive polypeptide materials prepared by ring‐opening polymerization of α‐amino acid N‐carboxyanhydrides

Zhang

2013

J Polym Sci B Polym Phys

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Design and synthesis of biodegradable stimuli-responsive polypeptides are important areas considering their promising applications in biomedical fields. This article summarizes the most recent progresses in the development of stimuli-responsive polypeptide materials prepared via ringopening polymerization of a-amino acid N-carboxyanhydrides. We discuss the design, synthesis and structure-property correlation of emerging materials including thermo-responsive, redox-responsive, photo-responsive and biomolecule responsive polypeptides. Considering the unique structural features of amino acids, we try to emphasize that the thermo-responsive properties not only depend on the amino acid structure but also rely on the secondary structures of polypeptides. V C 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part B: Polym. Phys. 2013, 51, 546-555

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Section: Biomolecule Responsive Polypeptidesmentioning

confidence: 99%

Stimuli‐responsive polypeptide materials prepared by ring‐opening polymerization of α‐amino acid N‐carboxyanhydrides

Zhang

2013

J Polym Sci B Polym Phys

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“…Well‐defined, high‐molecular‐weight lysine‐based homoglycopolypeptides and α‐mannose conjugated PLLys combined independently with PLLys or α‐galactose‐conjugated PLLys block glycocopolypeptides were produced that may emulate natural high molecular weight glycoproteins. Pati et al100 created an O ‐glycosylated lysine‐NCA possessing benzoate‐protected glucose units to a high reaction yield. Primary amine‐initiated polymerization of p ‐methoxybenzyl‐ L ‐glutamate (PMBn‐glu) followed sequentially by the ROP of the glycosylated NCA generated diblock glycocopolypeptides with a PDI of 1.15.…”

Section: Functionalization Of Block Copolypeptides Made By Nca Ropmentioning

confidence: 99%

“…(a) HAuCl 4 , CH 2 Cl 2 , rt, 0.5 h, 4 Å MS powder; (b) Pd/C, H 2 , 400 psi, CH3OH, 12 h; (c) triphosgene, THF, α‐pinene, 70°C. Reproduced with permission 100. Copyright 2011, The Royal Society of Chemistry.…”

Section: Functionalization Of Block Copolypeptides Made By Nca Ropmentioning

confidence: 99%

Block Copolypeptides Prepared by N‐Carboxyanhydride Ring‐Opening Polymerization

Habraken

Heise

Thornton

2012

Macromol. Rapid Commun.

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N-Carboxyanhydride ring-opening polymerization (NCA ROP) is a synthetically straightforward methodology to generate homopolypeptides. Extensive control over the polymerization permits the production of highly monodisperse synthetic polypeptides to a targeted molecular weight in the absence of unfavorable side reactions. Sequential NCA ROP permits the creation of block copolypeptides composed of individual polypeptide blocks boasting different functionalities, secondary structures, and desirable chemical properties. Consequently, a plethora of novel materials have been generated that have found wide-range applicability. This review offers an insight into contemporary synthetic approaches toward NCA ROP before highlighting a number of block copolypeptide architectures generated.

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“…Glycoconjugated poly(amino acids) (glycopolypeptides) are promising alternatives due to their high structural resemblance of natural glycoproteins. Recent advances in their synthesis from amino acid N ‐carboxyanhydride (NCA) make these synthetic glycopolypeptides readily available . Previously, the selective Concanavalin A (ConA) lectin binding of these synthetic glycopolypeptides, in aqueous solution, has been demonstrated by turbidity assays.…”

Section: Introductionmentioning

confidence: 99%

Synthetic Glycopolypeptides as Potential Inhibitory Agents for Dendritic Cells and HIV‐1 Trafficking

Huang

Zhang

et al. 2013

Macromol. Rapid Commun.

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Multivalent binding is a key for many critical biological processes and unique recognition and specificity in binding enables many of different glycans and proteins to work in a great harmony within the human body. In this study, the binding kinetics of synthetic glycopolypeptides to the dendritic cell lectin DC‐SIGN and their inhibition potential for DC‐SIGN interactions with the gp120 envelope glycoprotein of HIV‐1 (gp120) are investigated.

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Synthesis of glycopolypeptides by the ring opening polymerization of O-glycosylated-α-amino acid N-carboxyanhydride (NCA)

Cited by 54 publications

References 26 publications

Stimuli‐responsive polypeptide materials prepared by ring‐opening polymerization of α‐amino acid N‐carboxyanhydrides

Stimuli‐responsive polypeptide materials prepared by ring‐opening polymerization of α‐amino acid N‐carboxyanhydrides

Block Copolypeptides Prepared by N‐Carboxyanhydride Ring‐Opening Polymerization

Synthetic Glycopolypeptides as Potential Inhibitory Agents for Dendritic Cells and HIV‐1 Trafficking

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