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MedKoo Cat#: 597475 | Name: Glycylleucine
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Description:

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

Glycylleucine is a substrate for the assay of glycyl-L-leucine dipeptidase.

Chemical Structure

Glycylleucine
Glycylleucine
CAS#869-19-2

Theoretical Analysis

MedKoo Cat#: 597475

Name: Glycylleucine

CAS#: 869-19-2

Chemical Formula: C8H16N2O3

Exact Mass: 188.1161

Molecular Weight: 188.23

Elemental Analysis: C, 51.05; H, 8.57; N, 14.88; O, 25.50

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 #
No Data
Synonym
Glycylleucine; Glycyl-L-leucine; N-Glycyl-L-leucine; H-Gly-Leu-OH; Gly-Leu; NSC 83257; NSC-83257; NSC83257;
IUPAC/Chemical Name
(2S)-2-[(2-aminoacetyl)amino]-4-methylpentanoic acid
InChi Key
DKEXFJVMVGETOO-LURJTMIESA-N
InChi Code
InChI=1S/C8H16N2O3/c1-5(2)3-6(8(12)13)10-7(11)4-9/h5-6H,3-4,9H2,1-2H3,(H,10,11)(H,12,13)/t6-/m0/s1
SMILES Code
CC(C)C[C@@H](C(O)=O)NC(CN)=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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Glycyl-l-leucine is a dipeptide that can be a common substrate for glycyl-leucine dipeptidase.
In vitro activity:
This study has now investigated which peptides can aid the in vitro folding of class I molecules, and this study finds that the dipeptide glycyl-leucine efficiently supports the folding of HLA-A*02:01 and H-2K(b) into a peptide-receptive conformation that rapidly binds high-affinity peptides. Treatment of cells with glycyl-leucine induces accumulation of peptide-receptive H-2K(b) and HLA-A*02:01 at the surface of cells. Reference: Proc Natl Acad Sci U S A. 2013 Sep 17;110(38):15383-8. https://pubmed.ncbi.nlm.nih.gov/24003162/
In vivo activity:
The induction of diabetes caused a reduction in bodyweight in the DI mice, whereas in the CON group the bodyweight was significantly elevated in ascending order from day 1 to day 12 (Figure 3). The injection of all peptides (except for peptides A, B and G) and also DMSO prevented bodyweight loss. Peptide D (glycylleucine) was the most efficient at preventing bodyweight loss. Reference: J Diabetes Investig. 2019 Sep;10(5):1177-1188. https://pubmed.ncbi.nlm.nih.gov/30710452/
Solvent mg/mL mM
Solubility
Water 25.0 132.82
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 188.23 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
Formulation protocol:
1. Saini SK, Ostermeir K, Ramnarayan VR, Schuster H, Zacharias M, Springer S. Dipeptides promote folding and peptide binding of MHC class I molecules. Proc Natl Acad Sci U S A. 2013 Sep 17;110(38):15383-8. doi: 10.1073/pnas.1308672110. Epub 2013 Sep 3. PMID: 24003162; PMCID: PMC3780906. 2. Vahdatpour T, Nokhodchi A, Zakeri-Milani P, Mesgari-Abbasi M, Ahmadi-Asl N, Valizadeh H. Leucine-glycine and carnosine dipeptides prevent diabetes induced by multiple low-doses of streptozotocin in an experimental model of adult mice. J Diabetes Investig. 2019 Sep;10(5):1177-1188. doi: 10.1111/jdi.13018. Epub 2019 Mar 12. PMID: 30710452; PMCID: PMC6717823.
In vitro protocol:
1. Saini SK, Ostermeir K, Ramnarayan VR, Schuster H, Zacharias M, Springer S. Dipeptides promote folding and peptide binding of MHC class I molecules. Proc Natl Acad Sci U S A. 2013 Sep 17;110(38):15383-8. doi: 10.1073/pnas.1308672110. Epub 2013 Sep 3. PMID: 24003162; PMCID: PMC3780906.
In vivo protocol:
1. Vahdatpour T, Nokhodchi A, Zakeri-Milani P, Mesgari-Abbasi M, Ahmadi-Asl N, Valizadeh H. Leucine-glycine and carnosine dipeptides prevent diabetes induced by multiple low-doses of streptozotocin in an experimental model of adult mice. J Diabetes Investig. 2019 Sep;10(5):1177-1188. doi: 10.1111/jdi.13018. Epub 2019 Mar 12. PMID: 30710452; PMCID: PMC6717823.
1: Lochs H, Williams PE, Morse EL, Abumrad NN, Adibi SA. Metabolism of glycylleucine and its constituent amino acids by liver, muscle, kidney and gut in conscious dogs. Beitr Infusionther Klin Ernahr. 1987;17:167-70. PubMed PMID: 3689302. 2: Lochs H, Williams PE, Morse EL, Abumrad NN, Adibi SA. Metabolism of dipeptides and their constituent amino acids by liver, gut, kidney, and muscle. Am J Physiol. 1988 May;254(5 Pt 1):E588-94. PubMed PMID: 3364562. 3: Fok KF, Yankeelov JA Jr. Peptide-gap inhibitors: I. Competitive inhibition of aminopeptidase M by a hydrolytically resistant dipeptide analogue of glycylleucine. Biochem Biophys Res Commun. 1977 Jan 10;74(1):273-8. PubMed PMID: 836284. 4: Latal A, Degovics G, Epand RF, Epand RM, Lohner K. Structural aspects of the interaction of peptidyl-glycylleucine-carboxyamide, a highly potent antimicrobial peptide from frog skin, with lipids. Eur J Biochem. 1997 Sep 15;248(3):938-46. PubMed PMID: 9342250. 5: Adibi SA. Intestinal transport of dipeptides in man: relative importance of hydrolysis and intact absorption. J Clin Invest. 1971 Nov;50(11):2266-75. PubMed PMID: 5096512; PubMed Central PMCID: PMC292168. 6: Lee AJ, Beno DW, Zhang X, Shapiro R, Mason M, Mason-Bright T, Surber B, Edens NK. A (14)C-leucine absorption, distribution, metabolism and excretion (ADME) study in adult Sprague-Dawley rat reveals β-hydroxy-β-methylbutyrate as a metabolite. Amino Acids. 2015 May;47(5):917-24. doi: 10.1007/s00726-015-1920-6. Epub 2015 Jan 25. PubMed PMID: 25618754; PubMed Central PMCID: PMC4412734. 7: Adibi SA, Soleimanpour MR. Functional characterization of dipeptide transport system in human jejunum. J Clin Invest. 1974 May;53(5):1368-74. PubMed PMID: 4825229; PubMed Central PMCID: PMC302625. 8: Raghunath M, Morse EL, Adibi SA. Mechanism of clearance of dipeptides by perfused hindquarters: sarcolemmal hydrolysis of peptides. Am J Physiol. 1990 Oct;259(4 Pt 1):E463-9. PubMed PMID: 2221047. 9: Bhowmik SK, Ramirez-Peña E, Arnold JM, Putluri V, Sphyris N, Michailidis G, Putluri N, Ambs S, Sreekumar A, Mani SA. EMT-induced metabolite signature identifies poor clinical outcome. Oncotarget. 2015 Dec 15;6(40):42651-60. doi: 10.18632/oncotarget.4765. PubMed PMID: 26315396; PubMed Central PMCID: PMC4767460. 10: Marek A, Tureček F. Collision-induced dissociation of diazirine-labeled peptide ions. Evidence for Brønsted-acid assisted elimination of nitrogen. J Am Soc Mass Spectrom. 2014 May;25(5):778-89. doi: 10.1007/s13361-014-0832-0. Epub 2014 Feb 19. PubMed PMID: 24549894. 11: Josefsson L, Sjöström H, Norén O. Intracellular hydrolysis of peptides. Ciba Found Symp. 1977;(50):199-207. PubMed PMID: 244384. 12: Radhakrishnan AN. Intestinal dipeptidases and the dipeptide transport in the monkey and in man. Ciba Found Symp. 1977;(50):37-59. PubMed PMID: 413702. 13: Hama T, Tamaki N, Miyamoto F, Kita M, Tsunemori F. Intestinal absorption of beta-alanine, anserine and carnosine in rats. J Nutr Sci Vitaminol (Tokyo). 1976;22(2):147-57. PubMed PMID: 956928. 14: Norén O, Dabelsteen E, Sjöström H, Josefsson L. Histological localization of two dipeptidases in the pig small intestine and liver, using immunofluorescence. Gastroenterology. 1977 Jan;72(1):87-92. PubMed PMID: 318584. 15: Law BA. Peptide utilization by group N streptococci. J Gen Microbiol. 1978 Mar;105(1):113-8. PubMed PMID: 416171. 16: FLEISHER GA, BUTT HR, HUIZENGA KA. Enzymatic hydrolysis of L-leucylglycine in serum in hepatic disease. Proc Staff Meet Mayo Clin. 1957 Aug 7;32(16):410-24. PubMed PMID: 13465820. 17: Saini SK, Ostermeir K, Ramnarayan VR, Schuster H, Zacharias M, Springer S. Dipeptides promote folding and peptide binding of MHC class I molecules. Proc Natl Acad Sci U S A. 2013 Sep 17;110(38):15383-8. doi: 10.1073/pnas.1308672110. Epub 2013 Sep 3. PubMed PMID: 24003162; PubMed Central PMCID: PMC3780906. 18: Khelifa N, Brik M, Tessedre AC, De Rocquigny H, Roques BP, Courtieu J, Rimbault A. Cleavage of L-leucine-containing dipeptides by Clostridium butyricum. Bioorg Med Chem Lett. 1999 Jan 4;9(1):109-12. PubMed PMID: 9990466. 19: Kiyotani T, Sugawara Y. L-Leucylglycine 0.67-hydrate and [(4S)-2,2-dimethyl-4-(2-methylpropyl)-5-oxoimidazolidin-3-ium-1-yl]acetate. Acta Crystallogr C. 2012 Dec;68(Pt 12):o498-501. doi: 10.1107/S010827011204810X. Epub 2012 Nov 28. PubMed PMID: 23221255. 20: Tobey NA, Lyn-Cook LE, Ulshen MH, Heizer WD. Intestinal brush border peptidases: activities in normal and abnormal peroral intestinal biopsy specimens. J Lab Clin Med. 1986 Mar;107(3):221-7. PubMed PMID: 2869093.