γ-polyglutamic acid

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Structural formula
Structural formula γ-polyglutamic acid
General
Surname Polyglutamate
other names
  • Polyglutamic acid
  • Poly-γ-glutamate
  • Poly-γ-glutamic acid
CAS number 25736-27-0
properties
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

γ-polyglutamic acid or poly-gamma-glutamic acid , abbreviated γ-PGS (a polyglutamic acid, abbreviated PGS ), is a naturally occurring biopolymer in various organisms . α-PGS is only accessible synthetically.

properties

The peptide bond in γ-PGS is located between the amino group of glutamic acid and the carboxy group at the end of the glutamic acid side chain . γ-PGS is a main component of the slimy substance that forms when the Japanese food natto is prepared . γ-PGS is synthesized by bacteria , archaea and cnidaria and is used by these organisms as a slimy protective layer, glue and possibly as reserve material.

Short γ-polyglutamic acid chains ( oligomers ) arise briefly as a degradation product in the metabolism of many living organisms, when tetrahydrofolic acid polyglutamate is broken down by the enzyme gamma glutamyl hydrolase ( EC  3.4.19.9 ). But they are immediately further broken down into the glutamic acid components.

Some bacterial polyglutamates are made as a non-ribosomal peptide .

use

Polyglutamic acid is interesting for the pharmaceutical industry on the one hand because of its immunological neutrality as packaging for drugs, on the other hand immunization with polyglutamic acids could facilitate the fight against infection. PGS is used as a humectant in the food and cosmetics industries.

Methotrexate polyglutamates are the stable metabolites of methotrexate .

Polyglutamate is a main component of the Japanese food natto .

Individual evidence

  1. ↑ Data sheet Poly-L-γ-glutamic acid sodium salt from Sigma-Aldrich , accessed on November 12, 2014 ( PDF ).
  2. ↑ H. Poo, C. Park, MS Kwak, DY Choi, SP Hong, IH Lee, YT Lim, YK Choi, SR Bae, H. Uyama, CJ Kim, MH Sung: New biological functions and applications of high-molecular- mass poly-gamma-glutamic acid. In: Chemistry & biodiversity. Volume 7, number 6, June 2010, pp. 1555–1562, doi : 10.1002 / cbdv.200900283 . PMID 20564573 .
  3. ↑ Ing-Lung Shi and Jane-Yii Wu: Biosynthesis and Application of Poly (γ-glutamic acid) . In: Rehm, Bernd (Ed.): Microbial Production of Biopolymers and Polymer Precursors: Applications and Perspectives . Horizon Scientific Press, Cambs, UK 2009, ISBN 1-904455-36-0 , pp. 101-153 .
  4. ↑ M. Ashiuchi: Microbial production and chemical transformation of poly-γ-glutamate. In: Microbial biotechnology. Volume 6, number 6, November 2013, pp. 664-674, doi : 10.1111 / 1751-7915.12072 . PMID 23855427 . PMC 3815933 (free full text).
  5. ^ A b I. Bajaj, R. Singhal: Poly (glutamic acid) - an emerging biopolymer of commercial interest. In: Bioresource Technology . Volume 102, number 10, May 2011, pp. 5551-5561, doi : 10.1016 / j.biortech.2011.02.047 . PMID 21377358 .
  6. ↑ Y. Hamano, T. Arai, M. Ashiuchi, K. Kino: NRPSs and amide ligases producing homopoly (amino acid) s and homooligo (amino acid) s. In: Natural Product Reports . Volume 30, Number 8, August 2013, pp. 1087-1097, doi : 10.1039 / c3np70025a . PMID 23817633 .
  7. ↑ B. Manocha, A. Margaritis: Production and characterization of gamma-polyglutamic acid nanoparticles for controlled anticancer drug release. In: Critical reviews in biotechnology. Volume 28, Number 2, 2008, pp. 83-99, doi : 10.1080 / 07388550802107483 . PMID 18568849 .
  8. ↑ Buescher JM, Margaritis A: Microbial biosynthesis of polyglutamic acid biopolymer and applications in the biopharmaceutical, biomedical and food industries . In: Crit. Rev. Biotechnol. . 27, No. 1, 2007, pp. 1-19. doi : 10.1080 / 07388550601166458 . PMID 17364686 .
  9. ↑ Manocha B, Margaritis A: Production and characterization of gamma-polyglutamic acid nanoparticles for controlled anticancer drug release . In: Crit. Rev. Biotechnol. . 28, No. 2, 2008, pp. 83-99. doi : 10.1080 / 07388550802107483 . PMID 18568849 .
  10. ↑ S. Goodman: Measuring methotrexate polyglutamates. In: Clinical and Experimental Rheumatology . Volume 28, Number 5 Suppl 61, 2010 Sep-Oct, pp. S24-S26, PMID 21044429 .

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