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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:
556-33-2
Molecular Weight:
189.17
Beilstein:
1711130
EC Number:
209-122-0
MDL number:
MFCD00036223
UNSPSC Code:
12352209
PubChem Substance ID:
57651245
NACRES:
NA.26

product name

Gly-Gly-Gly, BioUltra, ≥99.0% (NT)

product line

BioUltra

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.

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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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
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
John M Antos et al.
The Journal of biological chemistry, 284(23), 16028-16036 (2009-04-11)
Folding and stability are parameters that control protein behavior. The possibility of conferring additional stability on proteins has implications for their use in vivo and for their structural analysis in the laboratory. Cyclic polypeptides ranging in size from 14 to
H V Alexandru
Annals of the New York Academy of Sciences, 1161, 387-396 (2009-05-12)
Triglycine sulfate (TGS) crystal is an important ferroelectric crystal used on a large spectrum of radiation detection. Crystals from this family are used as targeted vidicon materials. Pure, (L + D) and L- or D-alanine doped TGS crystals in the
Liang Ma et al.
Biochemistry, 49(9), 1954-1962 (2010-02-04)
To improve our understanding of the effects of small solutes on protein stability, we conducted atomistic simulations to quantitatively characterize the interactions between two broadly used small solutes, urea and glycine betaine (GB), and a triglycine peptide, which is a
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