Gly-Gly-Phe-OH
Need Assistance?
  • US & Canada:
    +
  • UK: +

Gly-Gly-Phe-OH

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Gly-Gly-Phe-OH is a cleavable peptide linker that is widely used in the development of antibody-drug conjugates. Furthermore, Gly-Gly-Phe-OH brings hope to the field of oncology research, having demonstrated its ability as a targeted therapeutic moiety to selectively target tumor cells with high precision.

Category
Others
Catalog number
BAT-005017
CAS number
6234-26-0
Molecular Formula
C13H17N3O4
Molecular Weight
279.30
Gly-Gly-Phe-OH
IUPAC Name
(2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-phenylpropanoic acid
Synonyms
Glycyl-glycyl-L-phenylalanine
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.296±0.06 g/cm3(Predicted)
Melting Point
228-230 °C (dec.)
Boiling Point
647.1±55.0 °C(Predicted)
Storage
Store at -20°C
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
InChI Key
KAJAOGBVWCYGHZ-JTQLQIEISA-N
Canonical SMILES
C1=CC=C(C=C1)CC(C(=O)O)NC(=O)CNC(=O)CN
1. β-Sheet to Helical-Sheet Evolution Induced by Topochemical Polymerization: Cross-α-Amyloid-like Packing in a Pseudoprotein with Gly-Phe-Gly Repeats
Kuntrapakam Hema, Kana M Sureshan Angew Chem Int Ed Engl. 2020 Jun 2;59(23):8854-8859. doi: 10.1002/anie.201914975. Epub 2020 Mar 25.
Protein-mimics are of great interest for their structure, stability, and properties. We are interested in the synthesis of protein-mimics containing triazole linkages as peptide-bond surrogate by topochemical azide-alkyne cycloaddition (TAAC) polymerization of azide- and alkyne-modified peptides. The rationally designed dipeptide N3 -CH2 CO-Phe-NHCH2 CCH (1) crystallized in a parallel β-sheet arrangement and are head-to-tail aligned in a direction perpendicular to the β-sheet-direction. Upon heating, crystals of 1 underwent single-crystal-to-single-crystal polymerization forming a triazole-linked pseudoprotein with Gly-Phe-Gly repeats. During TAAC polymerization, the pseudoprotein evolved as helical chains. These helical chains are laterally assembled by backbone hydrogen bonding in a direction perpendicular to the helical axis to form helical sheets. This interesting helical-sheet orientation in the crystal resembles the cross-α-amyloids, where α-helices are arranged laterally as sheets.
2. A systematic study of the valence electronic structure of cyclo(Gly-Phe), cyclo(Trp-Tyr) and cyclo(Trp-Trp) dipeptides in the gas phase
Elena Molteni, et al. Phys Chem Chem Phys. 2021 Dec 8;23(47):26793-26805. doi: 10.1039/d1cp04050b.
The electronic energy levels of cyclo(glycine-phenylalanine), cyclo(tryptophan-tyrosine) and cyclo(tryptophan-tryptophan) dipeptides are investigated with a joint experimental and theoretical approach. Experimentally, valence photoelectron spectra in the gas phase are measured using VUV radiation. Theoretically, we first obtain low-energy conformers through an automated conformer-rotamer ensemble sampling scheme based on tight-binding simulations. Then, different first principles computational schemes are considered to simulate the spectra: Hartree-Fock (HF), density functional theory (DFT) within the B3LYP approximation, the quasi-particle GW correction, and the quantum-chemistry CCSD method. Theory allows assignment of the main features of the spectra. A discussion on the role of electronic correlation is provided, by comparing computationally cheaper DFT scheme (and GW) results with the accurate CCSD method.
Online Inquiry
Verification code
Inquiry Basket