General Route toward Side-Chain-Functionalized α-Helical Polypeptides

A series of poly(γ-chloropropyl-l-glutamate) (PCPLG) with controlled polymer molecular weight (MW = 5−28 kg·mol−1) and molecular weight distribution (PDI = 1.16−1.26) have been prepared from hexamethyldisilazane (HMDS)-mediated ring-opening polymerization (ROP) of γ-chloropropyl-l-glutamic acid base...

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Published inBiomacromolecules Vol. 11; no. 6; pp. 1585 - 1592
Main Authors Tang, Haoyu, Zhang, Donghui
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 14.06.2010
Amer Chemical Soc
Subjects
Aminoacid polymers
Applied sciences
Biochemistry & Molecular Biology
Chemistry
Chemistry, Organic
Circular Dichroism
Exact sciences and technology
Life Sciences & Biomedicine
Magnetic Resonance Spectroscopy
Mannose - chemistry
Molecular Weight
Organosilicon Compounds - chemistry
Peptides - chemical synthesis
Peptides - chemistry
Physical Sciences
Physicochemistry of polymers
Polyglutamic Acid - analogs & derivatives
Polyglutamic Acid - chemical synthesis
Polyglutamic Acid - chemistry
Polymer Science
Protein Conformation
Science & Technology
Solutions
Synthetic biopolymers
DESIGN
1ST SYNTHESIS
GLYCOPOLYMERS
CLICK CHEMISTRY
FOLDAMERS
DYNAMICS
RING-OPENING POLYMERIZATION
COPOLYMERS
N-CARBOXYANHYDRIDES
COMBINATION
Ring opening polymerization
1,3-Dipolar cycloaddition
Alkyl glutamate polymer
Aldose
Experimental study
Aminoacid polymer
Thermal stability
Organic solution
Glycopolymer
Azides
Solid state
Monodispersed polymer
Chemical modification
Preparation
Soluble compound
Helical structure
Chlorine containing polymer
Aqueous solution
Nucleophilic substitution
Conformation
Online AccessGet full text

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Abstract A series of poly(γ-chloropropyl-l-glutamate) (PCPLG) with controlled polymer molecular weight (MW = 5−28 kg·mol−1) and molecular weight distribution (PDI = 1.16−1.26) have been prepared from hexamethyldisilazane (HMDS)-mediated ring-opening polymerization (ROP) of γ-chloropropyl-l-glutamic acid based N-carboxylanhydride (CP-NCA). CD, FTIR, and WAXS analysis reveal that the polymers adopt α-helical conformations both in solution and the solid state. Their helical surfaces can be readily decorated with functional moieties to confer desired properties, as demonstrated by the quantitative derivatization of the PCPLG side chains with azido functional groups that are amendable to “click” chemistry. Subsequent side-chain conjugation with mannose moieties via copper-mediated [2 + 3] alkyne−azide 1,3-dipolar cycloaddition affords water-soluble mannose−polypeptide conjugates with quantitative grafting efficiency occurring under mild conditions. CD analysis reveals that the mannose−polypeptide conjugates also retain α-helical conformations in aqueous solution.
AbstractList A series of poly(gamma-chloropropyl-L-glutamate) (PCPLG) with controlled polymer molecular weight (MW = 5-28 kg x mol(-1)) and molecular weight distribution (PDI = 1.16-1.26) have been prepared from hexamethyldisilazane (HMDS)-mediated ring-opening polymerization (ROP) of gamma-chloropropyl-L-glutamic acid based N-carboxylanhydride (CP-NCA). CD, FTIR, and WAXS analysis reveal that the polymers adopt alpha-helical conformations both in solution and the solid state. Their helical surfaces can be readily decorated with functional moieties to confer desired properties, as demonstrated by the quantitative derivatization of the PCPLG side chains with azido functional groups that are amendable to "click" chemistry. Subsequent side-chain conjugation with mannose moieties via copper-mediated [2 + 3] alkyne-azide 1,3-dipolar cycloaddition affords water-soluble mannose-polypeptide conjugates with quantitative grafting efficiency occurring under mild conditions. CD analysis reveals that the mannose-polypeptide conjugates also retain alpha-helical conformations in aqueous solution.A series of poly(gamma-chloropropyl-L-glutamate) (PCPLG) with controlled polymer molecular weight (MW = 5-28 kg x mol(-1)) and molecular weight distribution (PDI = 1.16-1.26) have been prepared from hexamethyldisilazane (HMDS)-mediated ring-opening polymerization (ROP) of gamma-chloropropyl-L-glutamic acid based N-carboxylanhydride (CP-NCA). CD, FTIR, and WAXS analysis reveal that the polymers adopt alpha-helical conformations both in solution and the solid state. Their helical surfaces can be readily decorated with functional moieties to confer desired properties, as demonstrated by the quantitative derivatization of the PCPLG side chains with azido functional groups that are amendable to "click" chemistry. Subsequent side-chain conjugation with mannose moieties via copper-mediated [2 + 3] alkyne-azide 1,3-dipolar cycloaddition affords water-soluble mannose-polypeptide conjugates with quantitative grafting efficiency occurring under mild conditions. CD analysis reveals that the mannose-polypeptide conjugates also retain alpha-helical conformations in aqueous solution.
A series of poly(gamma-chloropropyl-L-glutamate) (PCPLG) with controlled polymer molecular weight (MW = 5-28 kg x mol(-1)) and molecular weight distribution (PDI = 1.16-1.26) have been prepared from hexamethyldisilazane (HMDS)-mediated ring-opening polymerization (ROP) of gamma-chloropropyl-L-glutamic acid based N-carboxylanhydride (CP-NCA). CD, FTIR, and WAXS analysis reveal that the polymers adopt alpha-helical conformations both in solution and the solid state. Their helical surfaces can be readily decorated with functional moieties to confer desired properties, as demonstrated by the quantitative derivatization of the PCPLG side chains with azido functional groups that are amendable to "click" chemistry. Subsequent side-chain conjugation with mannose moieties via copper-mediated [2 + 3] alkyne-azide 1,3-dipolar cycloaddition affords water-soluble mannose-polypeptide conjugates with quantitative grafting efficiency occurring under mild conditions. CD analysis reveals that the mannose-polypeptide conjugates also retain alpha-helical conformations in aqueous solution.
A series of poly(gamma-chloropropyl-L-glutamate) (PCPLG) with controlled polymer molecular weight (MW 5-28 kg.mol(-1)) and molecular weight distribution (PDI = 1.16-1.26) have been prepared from hexamethyldisilazane (HMDS)-mediated ring-opening polymerization (ROP) of gamma-chloropropyl-L-glutamic acid based N-carboxylan-hydride (CP-NCA). CD, FTIR, and WAXS analysis reveal that the polymers adopt alpha-helical conformations both in solution and the solid state. Their helical surfaces can be readily decorated with functional moieties to confer desired properties, as demonstrated by the quantitative derivatization of the PCPLG side chains with azido functional groups that are amendable to "click" chemistry. Subsequent side-chain conjugation with mannose moieties via copper-mediated [2 + 3] alkyne-azide 1,3-dipolar cycloaddition affords water-soluble mannose polypeptide conjugates with quantitative grafting efficiency occurring under mild conditions. CD analysis reveals that the mannose polypeptide conjugates also retain alpha-helical conformations in aqueous solution.
A series of poly(γ-chloropropyl-l-glutamate) (PCPLG) with controlled polymer molecular weight (MW = 5−28 kg·mol−1) and molecular weight distribution (PDI = 1.16−1.26) have been prepared from hexamethyldisilazane (HMDS)-mediated ring-opening polymerization (ROP) of γ-chloropropyl-l-glutamic acid based N-carboxylanhydride (CP-NCA). CD, FTIR, and WAXS analysis reveal that the polymers adopt α-helical conformations both in solution and the solid state. Their helical surfaces can be readily decorated with functional moieties to confer desired properties, as demonstrated by the quantitative derivatization of the PCPLG side chains with azido functional groups that are amendable to “click” chemistry. Subsequent side-chain conjugation with mannose moieties via copper-mediated [2 + 3] alkyne−azide 1,3-dipolar cycloaddition affords water-soluble mannose−polypeptide conjugates with quantitative grafting efficiency occurring under mild conditions. CD analysis reveals that the mannose−polypeptide conjugates also retain α-helical conformations in aqueous solution.
Author Tang, Haoyu
Zhang, Donghui
Author_xml – sequence: 1
  givenname: Haoyu
  surname: Tang
  fullname: Tang, Haoyu
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  givenname: Donghui
  surname: Zhang
  fullname: Zhang, Donghui
  email: dhzhang@lsu.edu
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https://www.ncbi.nlm.nih.gov/pubmed/20465286$$D View this record in MEDLINE/PubMed
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DocumentTitleAlternate Side-Chain-Functionalized α-Helical Polypeptides
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Issue 6
Keywords DESIGN
1ST SYNTHESIS
GLYCOPOLYMERS
CLICK CHEMISTRY
FOLDAMERS
DYNAMICS
RING-OPENING POLYMERIZATION
COPOLYMERS
N-CARBOXYANHYDRIDES
COMBINATION
Ring opening polymerization
1,3-Dipolar cycloaddition
Alkyl glutamate polymer
Aldose
Experimental study
Aminoacid polymer
Thermal stability
Organic solution
Glycopolymer
Azides
Solid state
Monodispersed polymer
Chemical modification
Preparation
Soluble compound
Helical structure
Chlorine containing polymer
Aqueous solution
Nucleophilic substitution
Conformation
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SSID ssj0009345
Score 2.3662558
Snippet A series of poly(γ-chloropropyl-l-glutamate) (PCPLG) with controlled polymer molecular weight (MW = 5−28 kg·mol−1) and molecular weight distribution (PDI =...
A series of poly(gamma-chloropropyl-L-glutamate) (PCPLG) with controlled polymer molecular weight (MW 5-28 kg.mol(-1)) and molecular weight distribution (PDI =...
A series of poly(gamma-chloropropyl-L-glutamate) (PCPLG) with controlled polymer molecular weight (MW = 5-28 kg x mol(-1)) and molecular weight distribution...
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SubjectTerms Aminoacid polymers
Applied sciences
Biochemistry & Molecular Biology
Chemistry
Chemistry, Organic
Circular Dichroism
Exact sciences and technology
Life Sciences & Biomedicine
Magnetic Resonance Spectroscopy
Mannose - chemistry
Molecular Weight
Organosilicon Compounds - chemistry
Peptides - chemical synthesis
Peptides - chemistry
Physical Sciences
Physicochemistry of polymers
Polyglutamic Acid - analogs & derivatives
Polyglutamic Acid - chemical synthesis
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Title General Route toward Side-Chain-Functionalized α-Helical Polypeptides
URI http://dx.doi.org/10.1021/bm1002174
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https://www.ncbi.nlm.nih.gov/pubmed/20465286
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Volume 11
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