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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

Quality Level

100

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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Jiyun Shi et al.
Bioconjugate chemistry, 20(4), 750-759 (2009-03-27)
Radiolabeled cyclic RGD (Arg-Gly-Asp) peptides represent a new class of radiotracers with potential for early tumor detection and noninvasive monitoring of tumor metastasis and therapeutic response in cancer patients. This article describes the synthesis of two cyclic RGD peptide dimer
Angelo Bella et al.
Angewandte Chemie (International ed. in English), 51(2), 428-431 (2011-11-25)
Two faces for one matrix: A single bifaceted cyclopeptide block forms highly branched, porous, and intricate fibrillar networks, which span microscopic dimensions and mimic the extracellular matrix to support cell growth and proliferation. The peptide block has two domains connected
Jiyun Shi et al.
Journal of medicinal chemistry, 51(24), 7980-7990 (2008-12-04)
This report describes the synthesis of two new cyclic RGD (Arg-Gly-Asp) dimers, 3 (E[G(3)-c(RGDfK)](2)) and 4 (G(3)-E[G(3)-c(RGDfK)](2)), and their corresponding conjugates 5 (HYNIC-E[G(3)-c(RGDfK)](2): HYNIC = 6-(2-(2-sulfonatobenzaldehyde)hydrazono)nicotinyl) and 6 (HYNIC-G(3)-E[G(3)-c(RGDfK)](2)). Integrin alpha(v)beta(3) binding affinities of 5 and 6 were determined by
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
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
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