Glycylglycine

Structural formula
General
Surname	Glycylglycine
other names	Diglycine; GlyGly; [(Aminoacetyl) amino] acetic acid; Glycyl Glycine; DIPEPTIDE-15 ( INCI ) ;
Molecular formula	C 4 H 8 N 2 O 3
External identifiers / databases
EC number	209-127-8
ECHA InfoCard	100.008.299
PubChem	11163
ChemSpider	10690
Wikidata	Q665455
properties
Molar mass	132.12 g mol −1
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 319
	P: 305-338-351
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Glycylglycine is the dipeptide of the amino acid glycine and therefore the simplest peptide .

Manufacturing

Glycylglycine was first produced in 1901 by Emil Fischer and Ernest Fourneau by boiling 2,5-diketopiperazine (synonym: glycine anhydride) with hydrochloric acid. It is also produced by alkaline solutions and many other processes.

use

Glycylglycine is used in biochemistry as a buffer in the pH ranges 2.5-3.8 and 7.5-8.9. In aqueous solutions it tends to hydrolyze . Glycylglycine is used as a buffer in the course of cell disruption to avoid inclusion bodies in protein purification . The sodium salt of glycylglycine is used in electrophoresis buffers in capillary electrophoresis . Glycylglycine is used as a starting material in peptide synthesis .

Glycylglycine is also used in cosmetics to give hair a softer feel .

Individual evidence

↑ Entry on DIPEPTIDE-15 in the CosIng database of the EU Commission, accessed on December 29, 2019.
↑ ^a ^b Datasheet GlycylGlycine - PharmaGrade, Manufactured under appropriate GMP controls for pharma or biopharmaceutical production at Sigma-Aldrich , accessed on August 1, 2016 ( PDF ).
^ ^A ^b Victor von Richter : R. Anschütz and G. Shroeter (eds.): Richter's organic chemistry , Translated and revised by Percy E. Spielman after Edgar F. Smith, 3rd American. Edition, Volume I. Chemistry of the aliphatic series, P. Blakiston's Son & Co., Philadelphia 1916, p. 391 (accessed July 15, 2010).
^ RHA Plimmer: The chemical composition of the proteins . Ed .: RHA Plimmer & FG Hopkins (= Monographs on biochemistry . Volume II ). 1st edition. 2008, ISBN 978-1-4097-9725-8 ( google.com - first edition: Longmans, Green and Co., London 1908).
↑ Max S. Dunn, AW Butler, T. Deakers: The synthesis of glycylglycine . In: American Society for Biochemistry and Molecular Biology (Ed.): Journal of Biological Chemistry . tape 99 , no. 1 , December 1, 1932, p. 217-220 ( jbc.org [PDF]).
^ Marshall E. Smith, Lynwood B. Smith: Piperazine Dihydrochloride and Glycylglycine as Non-Toxic Buffers in Distilled Water and in Sea Water. In: Biological Bulletin. 96, 1949, p. 233, doi: 10.2307 / 1538357 .
↑ S Ghosh, S Rasheedi, SS Rahim, S Banerjee, RK Choudhary, P Chakhaiyar, NZ Ehtesham, S Mukhopadhyay, SE Hasnain: Method for enhancing solubility of the expressed recombinant proteins in Escherichia coli . In: BioTechniques . 37, No. 3, 2004, pp. 418, 420, 422-3. PMID 15470897 .
↑ A. Zinellu, S. Sotgia, S. Caddeo, L. Deiana, C. Carru: Sodium glycylglycine as effective electrolyte run buffer for ascorbic and uric acid separation by CZE: a comparison with two other CE assays. In: Journal of Separation Science . Volume 28, Number 16, November 2005, pp. 2193-2199, PMID 16318217 .
↑ Susan Budavari (Ed.): The Merck Manual , 11th. Edition, Merck & Co., Rahway, NJ 1989, ISBN 0-911910-28-X , pp. 707-708.
^ S. Breakspear, M. Fukuhara, T. Itou, Y. Hirano, M. Nojiri, A. Kiyomine, S. Inoue: Alignment control and softness creation in hair with glycylglycine. In: Journal of Cosmetic Science . Volume 64, Number 1, 2013, pp. 19-33, PMID 23449128 .

[CosIng-1] Entry on DIPEPTIDE-15 in the CosIng database of the EU Commission, accessed on December 29, 2019.

[Sigma-2] Datasheet GlycylGlycine - PharmaGrade, Manufactured under appropriate GMP controls for pharma or biopharmaceutical production at Sigma-Aldrich , accessed on August 1, 2016 ( PDF ).

[richter-3] A ^b Victor von Richter : R. Anschütz and G. Shroeter (eds.): Richter's organic chemistry , Translated and revised by Percy E. Spielman after Edgar F. Smith, 3rd American. Edition, Volume I. Chemistry of the aliphatic series, P. Blakiston's Son & Co., Philadelphia 1916, p. 391 (accessed July 15, 2010).

[4] RHA Plimmer: The chemical composition of the proteins . Ed .: RHA Plimmer & FG Hopkins (= Monographs on biochemistry . Volume II ). 1st edition. 2008, ISBN 978-1-4097-9725-8 ( google.com - first edition: Longmans, Green and Co., London 1908).

[5] Max S. Dunn, AW Butler, T. Deakers: The synthesis of glycylglycine . In: American Society for Biochemistry and Molecular Biology (Ed.): Journal of Biological Chemistry . tape 99 , no. 1 , December 1, 1932, p. 217-220 ( jbc.org [PDF]).

[DOI10.2307/1538357-6] Marshall E. Smith, Lynwood B. Smith: Piperazine Dihydrochloride and Glycylglycine as Non-Toxic Buffers in Distilled Water and in Sea Water. In: Biological Bulletin. 96, 1949, p. 233, doi: 10.2307 / 1538357 .

[7] S Ghosh, S Rasheedi, SS Rahim, S Banerjee, RK Choudhary, P Chakhaiyar, NZ Ehtesham, S Mukhopadhyay, SE Hasnain: Method for enhancing solubility of the expressed recombinant proteins in Escherichia coli . In: BioTechniques . 37, No. 3, 2004, pp. 418, 420, 422-3. PMID 15470897 .

[8] A. Zinellu, S. Sotgia, S. Caddeo, L. Deiana, C. Carru: Sodium glycylglycine as effective electrolyte run buffer for ascorbic and uric acid separation by CZE: a comparison with two other CE assays. In: Journal of Separation Science . Volume 28, Number 16, November 2005, pp. 2193-2199, PMID 16318217 .

[9] Susan Budavari (Ed.): The Merck Manual , 11th. Edition, Merck & Co., Rahway, NJ 1989, ISBN 0-911910-28-X , pp. 707-708.

[10] S. Breakspear, M. Fukuhara, T. Itou, Y. Hirano, M. Nojiri, A. Kiyomine, S. Inoue: Alignment control and softness creation in hair with glycylglycine. In: Journal of Cosmetic Science . Volume 64, Number 1, 2013, pp. 19-33, PMID 23449128 .