MedKoo Cat#: 597327 | Name: Diglycyl-histidine
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Description:

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

Diglycyl-histidine is a tripeptide complexed with cupric ion designed to mimic specific Cu(II) transport site of ascorbate on albumin molecule; glycylglycylhistamine is An amine derived by enzymatic decarboxylation of histidine.

Chemical Structure

Diglycyl-histidine
CAS#7451-76-5

Theoretical Analysis

MedKoo Cat#: 597327

Name: Diglycyl-histidine

CAS#: 7451-76-5

Chemical Formula: C10H15N5O4

Exact Mass: 269.1124

Molecular Weight: 269.26

Elemental Analysis: C, 44.61; H, 5.62; N, 26.01; O, 23.77

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
500mg USD 1,050.00 2 Weeks
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Related CAS #
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Synonym
Diglycyl-histidine; Gly-gly-his; Glycylglycyl-L-histidine; H-Gly-Gly-His-OH; NSC 334195; NSC-334195; NSC334195;
IUPAC/Chemical Name
glycylglycyl-L-histidine
InChi Key
PDAWDNVHMUKWJR-ZETCQYMHSA-N
InChi Code
InChI=1S/C10H15N5O4/c11-2-8(16)13-4-9(17)15-7(10(18)19)1-6-3-12-5-14-6/h3,5,7H,1-2,4,11H2,(H,12,14)(H,13,16)(H,15,17)(H,18,19)/t7-/m0/s1
SMILES Code
O=C(O)[C@H](CC1=CNC=N1)NC(CNC(CN)=O)=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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 269.26 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.

Recalculate based on batch purity %
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
1: Hu X, Zhang Q, Wang W, Yuan Z, Zhu X, Chen B, Chen X. Tripeptide GGH as the Inhibitor of Copper-Amyloid-β-Mediated Redox Reaction and Toxicity. ACS Chem Neurosci. 2016 Sep 21;7(9):1255-63. doi: 10.1021/acschemneuro.6b00145. Epub 2016 Aug 3. PubMed PMID: 27433833. 2: Gerlich M, Neumann S. MetFusion: integration of compound identification strategies. J Mass Spectrom. 2013 Mar;48(3):291-8. doi: 10.1002/jms.3123. PubMed PMID: 23494783. 3: Joyner JC, Hodnick WF, Cowan AS, Tamuly D, Boyd R, Cowan JA. Antimicrobial metallopeptides with broad nuclease and ribonuclease activity. Chem Commun (Camb). 2013 Mar 14;49(21):2118-20. doi: 10.1039/c3cc38977d. Epub 2013 Feb 5. PubMed PMID: 23380915; PubMed Central PMCID: PMC3632407. 4: Gruchlik A, Jurzak M, Chodurek E, Dzierzewicz Z. Effect of Gly-Gly-His, Gly-His-Lys and their copper complexes on TNF-alpha-dependent IL-6 secretion in normal human dermal fibroblasts. Acta Pol Pharm. 2012 Nov-Dec;69(6):1303-6. PubMed PMID: 23285694. 5: Matias AC, Villa dos Santos N, Chelegão R, Nomura CS, Fiorito PA, Cerchiaro G. Cu(GlyGlyHis) effects on MCF7 cells: copper uptake, reactive oxygen species generation and membrane topography changes. J Inorg Biochem. 2012 Nov;116:172-9. doi: 10.1016/j.jinorgbio.2012.07.012. Epub 2012 Aug 2. PubMed PMID: 23022694. 6: Lin M, Hu X, Ma Z, Chen L. Functionalized polypyrrole nanotube arrays as electrochemical biosensor for the determination of copper ions. Anal Chim Acta. 2012 Oct 9;746:63-9. doi: 10.1016/j.aca.2012.08.017. Epub 2012 Aug 23. PubMed PMID: 22975181. 7: Yokawa K, Kagenishi T, Kawano T. Prevention of oxidative DNA degradation by copper-binding peptides. Biosci Biotechnol Biochem. 2011;75(7):1377-9. Epub 2011 Jul 7. PubMed PMID: 21737913. 8: Lin M, Cho M, Choe WS, Yoo JB, Lee Y. Polypyrrole nanowire modified with Gly-Gly-His tripeptide for electrochemical detection of copper ion. Biosens Bioelectron. 2010 Oct 15;26(2):940-5. doi: 10.1016/j.bios.2010.06.030. Epub 2010 Jun 25. PubMed PMID: 20630738. 9: Lin M, Cho MS, Choe WS, Lee Y. Electrochemical analysis of copper ion using a Gly-Gly-His tripeptide modified poly(3-thiopheneacetic acid) biosensor. Biosens Bioelectron. 2009 Sep 15;25(1):28-33. doi: 10.1016/j.bios.2009.05.035. Epub 2009 Jun 6. PubMed PMID: 19560335. 10: Hamada H, Abe Y, Nagane R, Fang YY, Lewis MA, Long EC, Chikira M. DNA-fiber EPR investigation of the influence of amino-terminal residue stereochemistry on the DNA binding orientation of Cu(II).Gly-Gly-His-derived metallopeptides. J Inorg Biochem. 2007 Oct;101(10):1529-36. Epub 2007 Jul 3. PubMed PMID: 17706784; PubMed Central PMCID: PMC2140950. 11: Jones EA, Lockyer NP, Kordys J, Vickerman JC. Suppression and enhancement of secondary ion formation due to the chemical environment in static-secondary ion mass spectrometry. J Am Soc Mass Spectrom. 2007 Aug;18(8):1559-67. Epub 2007 May 24. PubMed PMID: 17604641. 12: Fang YY, Claussen CA, Lipkowitz KB, Long EC. Diastereoselective DNA cleavage recognition by Ni(II) x Gly-Gly-His-derived metallopeptides. J Am Chem Soc. 2006 Mar 15;128(10):3198-207. PubMed PMID: 16522100; PubMed Central PMCID: PMC2538425. 13: Alipázaga MV, Moreno RG, Linares E, Medeiros MH, Coichev N. Oxidative DNA damage induced by autoxidation of microquantities of S(IV) in the presence of Ni(II)-Gly-Gly-His. Dalton Trans. 2005 Dec 7;(23):3738-44. PubMed PMID: 16471054. 14: Van Dijk J, Lafont C, Knetsch ML, Derancourt J, Manstein DJ, Long EC, Chaussepied P. Conformational changes in actin-myosin isoforms probed by Ni(II).Gly-Gly-His reactivity. J Muscle Res Cell Motil. 2004;25(7):527-37. Epub 2005 Feb 9. PubMed PMID: 15711883. 15: Green BJ, Tesfai TM, Margerum DW. Nickel(III) oxidation of its glycylglycylhistamine complex. Dalton Trans. 2004 Nov 7;(21):3508-14. Epub 2004 Sep 20. PubMed PMID: 15510270. 16: Brown KC, Kodadek T. Protein cross-linking mediated by metal ion complexes. Met Ions Biol Syst. 2001;38:351-84. Review. PubMed PMID: 11219015. 17: Steullet V, Dixon DW. Design, synthesis and DNA-cleavage of Gly-Gly-His-naphthalene diimide conjugates. Bioorg Med Chem Lett. 1999 Oct 18;9(20):2935-40. PubMed PMID: 10571151. 18: Joshi PC. Copper(II) as an efficient scavenger of singlet molecular oxygen. Indian J Biochem Biophys. 1998 Aug;35(4):208-15. PubMed PMID: 9854900. 19: Brown KC, Yu Z, Burlingame AL, Craik CS. Determining protein-protein interactions by oxidative cross-linking of a glycine-glycine-histidine fusion protein. Biochemistry. 1998 Mar 31;37(13):4397-406. PubMed PMID: 9521759. 20: Dicks AP, Williams DL. Generation of nitric oxide from S-nitrosothiols using protein-bound Cu2+ sources. Chem Biol. 1996 Aug;3(8):655-9. PubMed PMID: 8807899.