Glycyl-L-glutamine
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Glycyl-L-glutamine
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CAS No:
13115-71-4
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Formula:
C7H13N3O4
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Chemical Name:
Glycyl-L-glutamine
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Synonyms:
L-Glutamine,glycyl-;Glutamine,N2-glycyl-,L-;L-Glutamine,N2-glycyl-;Glycyl-L-glutamine;105: PN: EP2161028 PAGE: 10 claimed protein;101: PN: WO2011146121 PAGE: 115 claimed sequence;143: PN: US20130123467 SEQID: 172 claimed protein;(2S)-2-(2-Aminoacetamido)-4-carbamoylbutanoic acid;(S)-5-Amino-2-(2-aminoacetamido)-5-oxopentanoic acid;(2S)-5-Amino-2-[(2-azaniumylacetyl)amino]-5-oxopentanoate;23: PN: WO2020009548 SEQID: 23 claimed protein;15: PN: WO2021055880 SEQID: 16 claimed protein
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CAS No:
Description
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[1]. Glycyl-glutamine (Glycyl-L-glutamine) is an activate and stable glutamine-containing neuropeptide over glutamine (Gln)[2].
Gly-Gln is a dipeptide formed from glycine and L-glutamine residues. It has a role as a metabolite and a protective agent. It is a tautomer of a Gly-Gln zwitterion.
Characteristics
136
-4.6
white crystals or crystalline powder
1.4±0.1 g/cm3
202-203 °C
643.1°C at 760 mmHg
342.7±31.5 °C
1.538
H2O: 154 g/L (20 ºC)
2-8°C
3.4E-18mmHg at 25°C
-6.5 º (c=10, 2N HCl)
Glycyl-L-glutamine Use and Manufacturing
General procedure: To a suspensionof 0.108 g (0.700 mmol) of 6-chloropurine or 0.119 g (0.700 mmol) of 2-amino-6-chloropurine in 3.0 mL of water we added 0.227 g (1.40 mmol) ofglycyl-(S)-serine, glycyl-(RS)-serine, or 0.284 g (1.40 mmol) of General procedure: To a suspensionof 0.108 g (0.700 mmol) of 6-chloropurine or 0.119 g (0.700 mmol) of 2-amino-6-chloropurine in 3.0 mL of water we added 0.227 g (1.40 mmol) ofglycyl-(S)-serine, glycyl-(RS)-serine, or 0.284 g (1.40 mmol) of Synthesis of (IX a)A solution of the commercial dipeptide Gly-Asn (22 mg, 0.11 mmol) in dioxane (150L) and water (250 pL) is added with Na2CO3 (26.5 mg) and FmocCl (31 mg, 1.3eq). The reaction is allowed to stir at room temperature for 1 6h, after which time it iscomplete. After the addition of water (5 ml), the solution is extracted with EtOAc (3 x 5 ml). The combined organic phases are then re-extracted with a saturated solution of NaHCO3 (3 x 5 ml), and the combined aqueous extracts are acidified to pH 1 by addition of 1M HC1 and then re-extracted with AcOEt (3 x 5 ml). The combinedorganic phases are dried over Na2SO4 and evaporated to dryness, thereby obtaining (IX a) in quantitative yield. 'H-NMR (400 MHz, D20, 6-H): 1.98 (m, 1H, Asn-f3), 2.18 (m, 1H, Asn-), 2.33 (m, 2H, Asn-y), 3.90 (m, 2H, Gly-ct), 4.23 (m, 1H), 4.31(m, 1H), 4.47 (dd, 1H, Asn-a), 7.31 (m, 2H, Ar), 7.38 (m, 2H, Ar), 7.69 (m, 2H, Ar), 7.81 (m, 2H, Ar).
Computed Properties
Molecular Weight:203.20
XLogP3:-4.6
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:203.09060590
Monoisotopic Mass:203.09060590
Topological Polar Surface Area:136
Heavy Atom Count:14
Complexity:241
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Provides glutamine to promote protein synthesis and is broken down into glycine and glutamine in the body.
Registered Holders
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Evonik Specialty Chemicals(Shanghai) Co., Ltd.
Active
China
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Jinyao Pharmaceutical Co., Ltd.
Active
China
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Shandong Weigao Pharmaceutical Co., Ltd.
Active
China
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