glycylglycyl-L-phenylalanine
Basic information
- CAS
6234-26-0- Standard SMILES
NCC(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)O- InChIKey
KAJAOGBVWCYGHZ-JTQLQIEISA-N- Molecular formula
- C13H17N3O4
- Average molar mass
- 279.29 g/mol
- Monoisotopic mass
- 279.12190602
Overview
Gly-Gly-Phe is a tripeptide composed of glycine, glycine and L-phenylalanine residues joined in sequence. It has a role as a metabolite.
Names & identifiers
- Preferred name
- glycylglycyl-L-phenylalanine
- IUPAC
- (2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-phenylpropanoic acid
- English name
- H-Gly-Gly-Phe-OH
- Molecular formula
- C13H17N3O4
- Molecular weight
- 279.29
Names & synonyms
6234-26-0glycylglycyl-L-phenylalanineDTXSID301308519RefChem:1086099DTXCID901738423H-GLY-GLY-PHE-OH(S)-2-(2-(2-Aminoacetamido)acetamido)-3-phenylpropanoic acidgly-gly-pheMFCD00066054L-N-(N-Glycylglycyl)-3-phenylalanineglycylglycylphenylalanine(2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-phenylpropanoic acid
Show more names
Gly-Gly-Phe-OHGly-Gly-L-Phe-OHEnkephalin (2-4)Human β-endorphin-(2-4)H-GLY-GLY-PHE-OH USP/EP/BPGly-Gly-Phe-OH≥ 95% (HPLC)
CHEMBL1221711Alanine, N-(N-glycylglycyl)-3-phenyl-, L-CHEBI:73905(2S)-2-[2-(2-AMINOACETAMIDO)ACETAMIDO]-3-PHENYLPROPANOIC ACIDGlycyl-glycyl-L-phenylalanine(S)-2-[2-(2-Aminoacetamido)acetamido]-3-phenylpropanoic AcidGly-Gly-L-Phe(2S)-2-[[2-[(2-azaniumylacetyl)amino]acetyl]amino]-3-phenylpropanoate
Database identifiers
- CAS
6234-26-0
Properties
Computed structural properties
- XLogP
- -3.1
- Topological polar surface area
- 122 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 7
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 354
Physicochemical properties
- Melting point
- 228 · 228-230 °C (decomp)
- Boiling point
- 647.1 · 647.1±55.0 °C(Predicted)
- Density
- 1.296 · 1.296±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C
- pka
- 3.47 · 3.47±0.10(Predicted)
- form
- Solid
- InChI
- InChI=1S/C13H17N3O4/c14-7-11(17)15-8-12(18)16-10(13(19)20)6-9-4-2-1-3-5-9/h1-5,10H,6-8,14H2,(H,15,17)(H,16,18)(H,19,20)/t10-/m0/s1
- InChIKey
- KAJAOGBVWCYGHZ-JTQLQIEISA-N
- SMILES
- C(O)(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CN
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
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
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
UsesH-Gly-Gly-Phe-OH is a tripeptide linker that may be used in the creation of antibody drug conjugates (ADCs). The N-terminal of the glycine tripeptide is free to perform a variety of reactions such as couplings with carboxylic acids or NHS esters.
Additional notes
DefinitionChEBI: A tripeptide composed of glycine, glycine and L-phenylalanine residues joined in sequence.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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