A new synthesis of poly-γ-<scp>D</scp>- and <scp>L</scp>-glutamic acid

Kovács, József; Schmit, G. N.; Johnson, Brian J.

doi:10.1139/v69-609

Cited by 8 publications

(1 citation statement)

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“…Thus, the preparation and characterization of poly(α-alkyl γ-glutamate)s, denominated PAAG- n with n standing for the number of carbon atoms in the alkyl side chainhave been reported for n ranging from 1 to 22. − Other poly(γ-glutamate)s bearing either benzyl or ethoxyalkyl side chains have also been reported. The chemical synthesis of poly(γ-glutamate)s from glutamic acid was well-established long ago by Hungarian researchers and has been recently revisited by Sanda et al, in a report describing the preparation of several poly(α-methyl γ-glutamate)s with different chain stereochemistry.…”

Section: Introductionmentioning

confidence: 99%

Poly(α-alkyl γ-glutamate)s of Microbial Origin. 2. On the Microstructure and Crystal Structure of Poly(α-ethyl γ-glutamate)s

Ilarduya

Ittobane²,

Bermúdez³

et al. 2002

Biomacromolecules

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The stereochemical microstructure and crystalline structure of nearly racemic poly(alpha-ethyl gamma,DL-glutamate) obtained by esterification of biosynthetic poly(gamma-glutamic acid) were examined by NMR, DSC, and powder X-ray diffraction. The two enantiomerically pure poly(alpha-ethyl gamma-glutamate)s, as well as the racemic stereocopolymers with random and alternating microstructure, were prepared by chemical synthesis and studied in parallel to help in the interpretation of the data. The (13)C NMR analysis revealed that biosynthetic poly(alpha-ethyl gamma,DL-glutamate) consists of a block stereocopolymer accompanied by minor amounts of a mixture of the two optically pure homopolymers. The polymer is crystalline, with a degree of crystallinity and crystal structure essentially similar to those displayed by the optically pure polymers but clearly different from the alternating copolymer. Conversely, the racemic stereocopolymer with a random microstructure prepared by chemical synthesis is amorphous. The crystal structure of the racemic mixture of the D- and L-homopolymers seems to be very close to that of the biosynthetic stereocopolymer, although some indications suggesting the existence of a stereocomplex were found.

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Section: Introductionmentioning

confidence: 99%

Poly(α-alkyl γ-glutamate)s of Microbial Origin. 2. On the Microstructure and Crystal Structure of Poly(α-ethyl γ-glutamate)s

Ilarduya

Ittobane²,

Bermúdez³

et al. 2002

Biomacromolecules

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Optically Active Polymers

Inomata

Abe

1999

The Wiley Database of Polymer Properties

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Conformational studies of anthrax polypeptide, subtilis polypeptide, and synthetic poly‐γ‐Lglutamic acid

1973

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SynopsisPoly-y-L-glutamic acid has been synthesized by the activated pentachlorophenyl ester polymerization method and the molecule weight of the polymer was found to be 16,000. Comparative conformational studies on the synthetic and on the native polyglutamic acid obtained from B. anthracis and B. subtilis were carried out using optical rotatory dispersion, circular dichroism, peptide absorption spectrum, and titration data. These results show that poly-y-glutamic acid does not exhibit any conformational order under the conditions of investigation. A t low degrees of ionization, restriction of conformational freedom via random "hypercoiling" of the chain appears likely.

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A new synthesis of poly-γ-D- and L-glutamic acid

Abstract: A new synthesis of native polyglutan~ic acid is described through the polycondensation of y-glutamylglutaniic acid-a,%'-di-1-butyl-y-pentachlorophenyl ester. This route eliminates the possibility of transpeptidation.

Cited by 8 publications

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Poly(α-alkyl γ-glutamate)s of Microbial Origin. 2. On the Microstructure and Crystal Structure of Poly(α-ethyl γ-glutamate)s

Poly(α-alkyl γ-glutamate)s of Microbial Origin. 2. On the Microstructure and Crystal Structure of Poly(α-ethyl γ-glutamate)s

Optically Active Polymers

Conformational studies of anthrax polypeptide, subtilis polypeptide, and synthetic poly‐γ‐Lglutamic acid

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