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50239

Sigma-Aldrich

Gly-Gly-Gly

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

Synonym(s):

Glycyl-glycyl-glycine, Triglycine

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About This Item

Linear Formula:
NH2CH2CONHCH2CONHCH2COOH
CAS Number:
Molecular Weight:
189.17
Beilstein/REAXYS Number:
1711130
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26

product name

Gly-Gly-Gly, BioUltra, ≥99.0% (NT)

product line

BioUltra

Quality Level

assay

≥99.0% (NT)

form

powder

technique(s)

ligand binding assay: suitable

impurities

insoluble matter, passes filter test

ign. residue

≤0.1% (as SO4)

loss

≤0.5% loss on drying, 110 °C

color

white

pH

4.5-6.0 (25 °C, 0.5 M in H2O)

solubility

H2O: 0.5 M at 20 °C, clear, colorless

anion traces

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

cation traces

Al: ≤5 mg/kg
As: ≤0.1 mg/kg
Ba: ≤50 mg/kg
Bi: ≤5 mg/kg
Ca: ≤20 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
Li: ≤5 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Mo: ≤5 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Sr: ≤5 mg/kg
Zn: ≤5 mg/kg

λ

0.5 M in H2O

UV absorption

λ: 260 nm Amax: 0.15
λ: 280 nm Amax: 0.10

SMILES string

NCC(=O)NCC(=O)NCC(O)=O

InChI

1S/C6H11N3O4/c7-1-4(10)8-2-5(11)9-3-6(12)13/h1-3,7H2,(H,8,10)(H,9,11)(H,12,13)

InChI key

XKUKSGPZAADMRA-UHFFFAOYSA-N

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Amino Acid Sequence

Gly-Gly-Gly

General description

Gly-Gly-Gly or triglycine is a flexible peptide linker with three glycine residues linked by peptide bonds in a linear sequence. Gly-linkers link multiple domains in a single protein without affecting the function of each domain.

Application

<ul>
<li><strong>Targeting PEPT1: a novel strategy to improve the antitumor efficacy of doxorubicin in human hepatocellular carcinoma therapy:</strong> Research explores Gly-Gly-Gly peptides as potential enhancers for drug transport efficiency, positioning them as valuable tools in clinical diagnostic peptide development for targeted cancer therapies (Gong et al., 2017).</li>
<li><strong>Iminopyridine complexes of manganese, rhenium, and molybdenum derived from amino ester methylserine and peptides Gly-Gly, Gly-Val, and Gly-Gly-Gly: self-assembly of the peptide chains:</strong> This study demonstrates the use of Gly-Gly-Gly in the synthesis of complex metal-peptide frameworks for potential use in high-purity peptide applications in IVD manufacturing (&Aacute;lvarez et al., 2012).</li>
</ul>

Biochem/physiol Actions

Substrate for reproducible serum protein measurements by the biuret reaction and for the assay of aminotripeptidases.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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USP

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1199308

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Iminodiacetic acid 98%

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Gly-Gly BioPerformance Certified, suitable for cell culture, &#8805;99%

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SAFC

G0674

GlycylGlycine

Vishnu Priyanka Reddy Chichili et al.
Protein science : a publication of the Protein Society, 22(2), 153-167 (2012-12-12)
Linkers or spacers are short amino acid sequences created in nature to separate multiple domains in a single protein. Most of them are rigid and function to prohibit unwanted interactions between the discrete domains. However, Gly-rich linkers are flexible, connecting
Chi-Kit Siu et al.
Journal of the American Society for Mass Spectrometry, 20(6), 996-1005 (2009-03-04)
Fragmentations of tautomers of the alpha-centered radical triglycine radical cation, [GGG(*)](+), [GG(*)G](+), and [G(*)GG](+), are charge-driven, giving b-type ions; these are processes that are facilitated by a mobile proton, as in the fragmentation of protonated triglycine (Rodriquez, C. F. et
Sudipta Chakraborty et al.
Bioconjugate chemistry, 21(5), 969-978 (2010-04-15)
This report presents the synthesis and evaluation of (111)In(DOTA-6G-RGD(4)) (DOTA = 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetracetic acid; 6G-RGD(4) = E{G(3)-E[G(3)-c(RGDfK)](2)}(2) and G(3) = Gly-Gly-Gly), (111)In(DOTA-RGD(4)) (RGD(4) = E{E[c(RGDfK)](2)}(2)) and (111)In(DOTA-3G-RGD(2)) (3G-RGD(2) = G(3)-E[G(3)-c(RGDfK)](2)) as new radiotracers for imaging integrin alpha(v)beta(3)-positive tumors. The IC(50) values
Avisek Chatterjee et al.
The Journal of chemical physics, 129(10), 105104-105104 (2008-12-03)
X-ray photoelectron spectroscopy (XPS) has been used to investigate the core-level electronic structures of glycine (G) and its peptides, including glycyl-glycine (GG), diglycyl-glycine (GGG), and polyglycine (poly-G), in their powder forms. Increasing the number of G units in the peptides
Craig P Schwartz et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(32), 14008-14013 (2010-07-28)
Nitrogen K-edge spectra of aqueous triglycine were measured using liquid microjets, and the effects of Hofmeister-active salts on the spectra were observed. Spectra simulated using density functional theory, sampled from room temperature classical molecular dynamics trajectories, capture all major features

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