Glycylglycylglycine zwitterion
Basic information
- CAS
556-33-2- Standard SMILES
[NH3+]CC(=O)NCC(=O)NCC(=O)[O-]- InChIKey
XKUKSGPZAADMRA-UHFFFAOYSA-N- Molecular formula
- C6H11N3O4
- Average molar mass
- 189.17 g/mol
- Monoisotopic mass
- 189.07495584
Overview
Gly-Gly-Gly zwitterion is a tripeptide zwitterion resulting from the transfer of a proton from the carboxy group to the amino group of Gly-Gly-Gly. Major microspecies at pH 7.3. It is a tautomer of a glycyl-glycyl-glycine.
Names & identifiers
- Preferred name
- Glycylglycylglycine zwitterion
- IUPAC
- 2-[[2-[(2-azaniumylacetyl)amino]acetyl]amino]acetate
- English name
- Glycyl-glycyl-glycine
- Molecular formula
- C6H11N3O4
- Molecular weight
- 189.17
Names & synonyms
GGG zwitterionGly-Gly-Gly zwitterionglycylglycylglycine zwitterionCHEBI:195214{[N-(azaniumylacetyl)glycyl]amino}acetateGLY-GLY-GLYH-GLY-GLY-GLY-OHGly-Gly-Gly-OHL-GLYCYL-GLYCYL-GLYCINE2-[[2-[(2-Aminoacetyl)amino]acetyl]amino]acetic acidH2N-GGG-OHTripeptide-44
Show more names
3-mer polyGlyTriglycine,99%DIGLYCYLGLYCINE
Database identifiers
- CAS
556-33-2- PubChem CID
- 6994044
- ChEBI
CHEBI:195214
Properties
Computed structural properties
- XLogP
- -2.9
- Topological polar surface area
- 126 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 210
Experimental & physicochemical properties
LogP-2.68
Solubility58.5 mg/mL at 25 °C
Melting Point246 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 240 · 240-250 °C
- Boiling point
- 324.41 °C · 324.41°C (rough estimate)
- Density
- 1.4204 · 1.4204 (rough estimate)
- refractive index
- 1.525 · 1.5250 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- 2 O: · H2O: 0.5 M at 20 °C, clear, colorless
- form
- Solid
- pka
- 3.225 · 3.225(at 25℃)
- color
- White to Off-White
- PH
- 4.5 · 4.5-6.0 (25℃, 0.5M in H2O)
- Water Solubility
- Soluble in water (94.6 mg/ml at 20°C), methanol (50 mg/ml), and 80% acetic acid (50 mg/ml).
- λmax
- 260 nm · λ: 260 nm Amax: 0.15λ: 280 nm Amax: 0.10
- Merck
- 14 · 14,6579
- BRN
- 1711130 · 1711130
- 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)
- InChIKey
- XKUKSGPZAADMRA-UHFFFAOYSA-N
- SMILES
- NCC(=O)NCC(=O)NCC(O)=O
- CAS DataBase Reference
- 556 · 556-33-2(CAS DataBase Reference)
- FDA UNII
- 73 ZDQ8B · CVK73ZDQ8B
- NIST Chemistry Reference
- N-(N-Glycylglycyl)glycine(556-33-2)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 26 · NA.26
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- WGK Germany
- 3 · 3
- F
- 3 · 3-10
- HS Code
- 29241990 · 29241990
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 3-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29241990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
UsesGlycyl-glycyl-glycine is used as a model peptide for studies of physicochemical parameters and molecular associations of small peptides. It is also used as a copper chelator and Substrate for tripeptide aminopeptidase.
General DescriptionGly-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.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: Glycyl-glycyl-glycine is a tripeptide in which three glycine units are linked via peptide bonds in a linear sequence. It is a tautomer of a Gly-Gly-Gly zwitterion.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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