Glycylglutamine | CAS#13115-71-4 | inhibitory neuropeptide

MedKoo Cat#: 597276 | Name: Glycylglutamine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Glycylglutamine is an inhibitory neuropeptide derived from beta-endorphin.

Chemical Structure

Glycylglutamine

CAS#13115-71-4

Theoretical Analysis

MedKoo Cat#: 597276

Name: Glycylglutamine

CAS#: 13115-71-4

Chemical Formula: C7H13N3O4

Exact Mass: 203.0906

Molecular Weight: 203.20

Elemental Analysis: C, 41.38; H, 6.45; N, 20.68; O, 31.49

Price and Availability

Size	Price	Availability	Quantity
5g	USD 250.00	2 Weeks
25g	USD 550.00	2 Weeks

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Related CAS #

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Synonym

Glycylglutamine; Glycyl glutamine; Glycyl-glutamine; Gly-gln; L-Glutamine, N2-glycyl-; Glycyl-l-glutamine; Gly-L-Gln; H-Gly-Gln-OH

IUPAC/Chemical Name

(2S)-5-amino-2-[(2-aminoacetyl)amino]-5-oxopentanoic acid

InChi Key

PNMUAGGSDZXTHX-BYPYZUCNSA-N

InChi Code

InChI=1S/C7H13N3O4/c8-3-6(12)10-4(7(13)14)1-2-5(9)11/h4H,1-3,8H2,(H2,9,11)(H,10,12)(H,13,14)/t4-/m0/s1

SMILES Code

O=C(O)[C@@H](NC(CN)=O)CCC(N)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Glycyl-glutamine (Glycyl-L-glutamine), as a enzymatic cleavage product of β-endorphin, is apparently an endogenous antagonist of beta-endorphin(1-31) in several systems. Glycyl-glutamine (Glycyl-L-glutamine) is an activate and stable glutamine-containing neuropeptide over glutamine (Gln).

In vitro activity:

TBD

In vivo activity:

Taken together, dietary Gly-Gln (gllycylglutamine) supplementation selectively modulated the gut microbiota, which may favor piglets' weaning-transition. These findings suggest that gut microbiota targeted approaches can be potentially used to improve weaning transition of piglets by dietary functional amino acid. Reference: Front Microbiol. 2020 Jan 28;10:3125. https://pubmed.ncbi.nlm.nih.gov/32117085/

	Solvent	mg/mL	mM
Solubility
	Water	62.5	307.58

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 203.20 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Yan Y, Xu B, Yin B, Xu X, Niu Y, Tang Y, Wang X, Xie C, Yang T, Zhou S, Yan X, Ma L. Modulation of Gut Microbial Community and Metabolism by Dietary Glycyl-Glutamine Supplementation May Favor Weaning Transition in Piglets. Front Microbiol. 2020 Jan 28;10:3125. doi: 10.3389/fmicb.2019.03125. PMID: 32117085; PMCID: PMC7025575. 2. Zhang Y, Yan H, Lv SG, Wang L, Liang GP, Wan QX, Peng X. Effects of glycyl-glutamine dipeptide supplementation on myocardial damage and cardiac function in rats after severe burn injury. Int J Clin Exp Pathol. 2013 Apr 15;6(5):821-30. PMID: 23638213; PMCID: PMC3638092.

In vitro protocol:

TBD

In vivo protocol:

1: Basaran NF, Buyukuysal RL, Sertac Yilmaz M, Aydin S, Cavun S, Millington WR. The effect of Gly-Gln [ß-endorphin30-31] on morphine-evoked serotonin and GABA efflux in the nucleus accumbens of conscious rats. Neuropeptides. 2016 Aug;58:23-9. doi: 10.1016/j.npep.2016.01.007. Epub 2016 Jan 28. PubMed PMID: 26861257. 2: Almashhadany A, Alghamdi OA, Van der Touw T, Jones GL, King N. L-Glycyl-L-glutamine provides the isolated and perfused young and middle-aged rat heart protection against ischaemia-reperfusion injury. Amino Acids. 2015 Aug;47(8):1559-65. doi: 10.1007/s00726-015-1997-y. Epub 2015 May 7. PubMed PMID: 25948163. 3: Cehak A, Schröder B, Feige K, Breves G. In vitro studies on intestinal peptide transport in horses. J Anim Sci. 2013 Nov;91(11):5220-8. doi: 10.2527/jas.2013-6325. Epub 2013 Sep 17. PubMed PMID: 24045491. 4: Zhang Y, Yan H, Lv SG, Wang L, Liang GP, Wan QX, Peng X. Effects of glycyl-glutamine dipeptide supplementation on myocardial damage and cardiac function in rats after severe burn injury. Int J Clin Exp Pathol. 2013 Apr 15;6(5):821-30. Print 2013. PubMed PMID: 23638213; PubMed Central PMCID: PMC3638092. 5: Bobba S, Resch GE, Gutheil WG. A liquid chromatography-tandem mass spectrometry assay for detection and quantitation of the dipeptide Gly-Gln in rat brain. Anal Biochem. 2012 Jun 15;425(2):145-50. doi: 10.1016/j.ab.2012.03.007. Epub 2012 Mar 21. PubMed PMID: 22446498; PubMed Central PMCID: PMC3613996. 6: Jiang JW, Ren ZG, Chen LY, Jiang L, Xie HY, Zhou L, Zheng SS. Enteral supplementation with glycyl-glutamine improves intestinal barrier function after liver transplantation in rats. Hepatobiliary Pancreat Dis Int. 2011 Aug;10(4):380-5. PubMed PMID: 21813386. 7: Leyton P, Saladino R, Crestini C, Campos-Vallette M, Paipa C, Berríos A, Fuentes S, Zárate RA. Influence of TiO2 on prebiotic thermal synthesis of the Gly-Gln polymer. Amino Acids. 2012 Jun;42(6):2079-88. doi: 10.1007/s00726-011-0939-6. Epub 2011 May 24. PubMed PMID: 21607746. 8: Renna MD, Oyadeyi AS, Bossi E, Kottra G, Peres A. Functional and structural determinants of reverse operation in the pH-dependent oligopeptide transporter PepT1. Cell Mol Life Sci. 2011 Sep;68(17):2961-75. doi: 10.1007/s00018-010-0604-3. Epub 2010 Dec 23. PubMed PMID: 21181229. 9: Bossi E, Renna MD, Sangaletti R, D'Antoni F, Cherubino F, Kottra G, Peres A. Residues R282 and D341 act as electrostatic gates in the proton-dependent oligopeptide transporter PepT1. J Physiol. 2011 Feb 1;589(Pt 3):495-510. doi: 10.1113/jphysiol.2010.200469. Epub 2010 Nov 29. PubMed PMID: 21115649; PubMed Central PMCID: PMC3055539. 10: Renna MD, Sangaletti R, Bossi E, Cherubino F, Kottra G, Peres A. Unified modeling of the mammalian and fish proton-dependent oligopeptide transporter PepT1. Channels (Austin). 2011 Jan-Feb;5(1):89-99. Epub 2011 Jan 1. PubMed PMID: 20953145. 11: Basaran NF, Buyukuysal RL, Millington WR, Cavun S. Glycyl-glutamine (beta-endorphin(30-31)) inhibits morphine-induced dopamine efflux in the nucleus accumbens. Naunyn Schmiedebergs Arch Pharmacol. 2010 May;381(5):467-75. doi: 10.1007/s00210-010-0507-8. Epub 2010 Mar 27. PubMed PMID: 20349045. 12: Jiang ZY, Sun LH, Lin YC, Ma XY, Zheng CT, Zhou GL, Chen F, Zou ST. Effects of dietary glycyl-glutamine on growth performance, small intestinal integrity, and immune responses of weaning piglets challenged with lipopolysaccharide. J Anim Sci. 2009 Dec;87(12):4050-6. doi: 10.2527/jas.2008-1120. Epub 2009 Aug 28. PubMed PMID: 19717785. 13: Cehak A, Burmester M, Geburek F, Feige K, Breves G. Electrophysiological characterization of electrolyte and nutrient transport across the small intestine in horses. J Anim Physiol Anim Nutr (Berl). 2009 Jun;93(3):287-94. doi: 10.1111/j.1439-0396.2008.00882.x. PubMed PMID: 19646103. 14: Luan S, Zhu Y, Jia Y. Synthesis and characterization of complex of glycyl-L-glutamine and bismuth trichloride. Protein Pept Lett. 2008;15(10):1094-9. PubMed PMID: 19075821. 15: Mertl M, Daniel H, Kottra G. Substrate-induced changes in the density of peptide transporter PEPT1 expressed in Xenopus oocytes. Am J Physiol Cell Physiol. 2008 Nov;295(5):C1332-43. doi: 10.1152/ajpcell.00241.2008. Epub 2008 Sep 17. PubMed PMID: 18799652. 16: Kottra G, Frey I, Daniel H. Inhibition of intracellular dipeptide hydrolysis uncovers large outward transport currents of the peptide transporter PEPT1 in Xenopus oocytes. Pflugers Arch. 2009 Feb;457(4):809-20. doi: 10.1007/s00424-008-0562-x. Epub 2008 Aug 29. PubMed PMID: 18758810. 17: Tóth B, Leonhard-Marek S, Hedrich HJ, Breves G. Characterisation of electrogenic nutrient absorption in the Cftr TgH(neoim)Hgu mouse model. J Comp Physiol B. 2008 Aug;178(6):705-12. doi: 10.1007/s00360-008-0259-7. Epub 2008 Mar 28. PubMed PMID: 18369642. 18: Resch GE, Simpson CW. Glycyl-glutamine reduces ethanol intake at three reward sites in P rats. Alcohol. 2008 Mar;42(2):99-106. doi: 10.1016/j.alcohol.2007.11.002. PubMed PMID: 18358988; PubMed Central PMCID: PMC2421011. 19: Lv SJ, Zhang Y, Sun Y, Wu W, You ZY, Wang SL, Peng X. [Protective effects of glycyl-glutamine dipeptide supplement on the heart function in burn rats]. Zhonghua Shao Shang Za Zhi. 2007 Aug;23(4):244-8. Chinese. PubMed PMID: 18095544. 20: Jiang JW, Zheng SS, Xue F, Gao LH, Jiang GP, Xie HY. Enteral feeding of glycyl-glutamine dipeptide improves the structure and absorptive function of the small intestine after allogenetic liver transplantation in rats. Hepatobiliary Pancreat Dis Int. 2006 May;5(2):199-204. PubMed PMID: 16698575.