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G5149

Sigma-Aldrich

Gly-Gln monohydrate

≥97% (HPLC), powder

Synonym(s):

Glycyl-L-glutamine

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About This Item

Empirical Formula (Hill Notation):
C7H13N3O4 · H2O
CAS Number:
172669-64-6
Molecular Weight:
221.21
MDL number:
MFCD00150855
UNSPSC Code:
12352209
PubChem Substance ID:
24895200
NACRES:
NA.32

product name

Gly-Gln monohydrate, ≥97% (HPLC)

Assay

≥97% (HPLC)

storage temp.

−20°C

SMILES string

O.NCC(=O)N[C@@H](CCC(N)=O)C(O)=O

InChI

1S/C7H13N3O4.H2O/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);1H2/t4-;/m0./s1

InChI key

KLFWVRQACSYLOH-WCCKRBBISA-N

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Amino Acid Sequence

Gly-Gln

General description

Glycyl-glutamine (gly-gln) is a dipeptide that is used as a substitute for glutamine in cell culture. Higher cell yields are obtained when this dipeptide is used instead of glutamine, where gly-gln affects substrate utilization and metabolism. Cell growth is higher as the concentrations of this dipeptide remain high, due to lower peptidase affinity.
Glycyl-glutamine is a dipeptide form of L-glutamine. Gly-Gln dipeptide exhibits enhanced solubility and thermostability. Moreover, this compound rapidly hydrolyzes into glutamine and glycine following intravenous infusion. Glycine can protect myocardial cells from ischemic injury by preventing cellular membrane permeability. Furthermore, the supplementation of glycyl-glutamine dipeptide proves advantageous for myocardial preservation in rats, as it enhances cardiocyte energy metabolism and augments ATP and glutathione synthesis.

Application

Gly-Gln monohydrate has been used:
  • as a supplement in Dulbecco′s modified Eagle medium (DMEM) to culture equine embryos
  • as a supplement in DMEM/F-12 to culture cleaved horse embryos
  • in the human tubal fluid (HTF) medium to study ammonium accumulation in commercially available embryo culture media during incubation and storage

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ammonium accumulation in commercially available embryo culture media and protein supplements during storage at 2-8 C and during incubation at 37 C
Kleijkers SHM, et al.
Human Reproduction, 31, 1192-1199 (2016)
Effects of glycyl-glutamine dipeptide supplementation on myocardial damage and cardiac function in rats after severe burn injury
Zhang Y, et al.
International Journal of Clinical and Experimental Pathology, 6, 821-821 (2013)
Parish, D.C. and Smyth, D.G.
Biochemical Society Transactions, 10, 221-221 (1982)
Culture protocols for horse embryos after ICSI: Effect of myo-inositol and time of media change
Brom-de-Luna JG, et al.
Animal Reproduction Science, 233, 106819-106819 (2021)
D C Parish et al.
Nature, 306(5940), 267-270 (1983-11-17)
The primary mechanism of activation of intracellular prohormones seems to involve proteolytic cleavage at sequences of consecutive basic residues. Thus, all the known biologically active peptides derived from the prohormone of corticotropin and beta-endorphin appear to be excised initially by
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