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50200

Sigma-Aldrich

Gly-Gly

≥99.0% (NT), suitable for ligand binding assays, BioXtra

Synonym(s):

Diglycine, Glycyl-glycine

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About This Item

Linear Formula:
NH2CH2CONHCH2COOH
CAS Number:
556-50-3
Molecular Weight:
132.12
Beilstein:
1765223
EC Number:
209-127-8
MDL number:
MFCD00008130
UNSPSC Code:
12161700
PubChem Substance ID:
329757576
NACRES:
NA.25

product name

Gly-Gly, BioXtra, ≥99.0% (NT)

product line

BioXtra

Quality Level

200

Assay

≥99.0% (NT)

form

powder

technique(s)

ligand binding assay: suitable

ign. residue

≤0.1% (as SO4)

loss

≤1% loss on drying, 110 °C

color

white

useful pH range

7.5-8.9

pKa (25 °C)

8.2

mp

220-240 °C (dec.)

solubility

H2O: 1 M at 20 °C, clear, colorless

anion traces

chloride (Cl-): ≤50 mg/kg
sulfate (SO42-): ≤50 mg/kg

cation traces

Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤50 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

SMILES string

NCC(=O)NCC(O)=O

InChI

1S/C4H8N2O3/c5-1-3(7)6-2-4(8)9/h1-2,5H2,(H,6,7)(H,8,9)

InChI key

YMAWOPBAYDPSLA-UHFFFAOYSA-N

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Biochem/physiol Actions

Glycine is a non-essential amino acid. Influx of calcium through the cell membrane is mediated by glycine-gated channel. Glycine participates in the synthesis of porphyrins, purine and serine. It also serves as a competitive agonist for glutamate in binding to the NMDA (N-methyl-D-aspartate) receptors. Glycine synthesis might be increased in rapidly proliferating cancer cells, due to increased demand for the amino acid. Diglycine is known to catalyze the formation of homo- and hetero dipeptides more efficiently than glycine.

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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Glycine and diglycine as possible catalytic factors in the prebiotic evolution of peptides.
Plankensteiner K
Origins of Life and Evolution of the Biosphere : the Journal of the International Society For the Study of the Origin of Life, 32(3), 225-236 (2002)
Metabolite Profiling Identifies a Key Role for Glycine in Rapid Cancer Cell Proliferation
Mohit Jain
Science, 336(6084), 1040-1044 (2012)
Francis Impens et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(34), 12432-12437 (2014-08-13)
SUMOylation is an essential ubiquitin-like modification involved in important biological processes in eukaryotic cells. Identification of small ubiquitin-related modifier (SUMO)-conjugated residues in proteins is critical for understanding the role of SUMOylation but remains experimentally challenging. We have set up a
Christopher M Leavitt et al.
Journal of the American Society for Mass Spectrometry, 22(11), 1941-1952 (2011-09-29)
We report vibrational predissociation spectra of the four protonated dipeptides derived from glycine and sarcosine, GlyGlyH(+)•(H(2))(1,2), GlySarH(+)•(D(2))(2), SarGlyH(+)•(H(2))(2), and SarSarH(+)•(D(2))(2), generated in a cryogenic ion trap. Sharp bands were recovered by monitoring photoevaporation of the weakly bound H(2) (D(2)) molecules
Namrata D Udeshi et al.
Molecular & cellular proteomics : MCP, 12(3), 825-831 (2012-12-26)
Detection of endogenous ubiquitination sites by mass spectrometry has dramatically improved with the commercialization of anti-di-glycine remnant (K-ε-GG) antibodies. Here, we describe a number of improvements to the K-ε-GG enrichment workflow, including optimized antibody and peptide input requirements, antibody cross-linking
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