Product Name: Boc-Gly-Gly-Phe-Gly-OH
Sequence: Boc-Gly-Gly-Phe-Gly-OH
Purity: 99%
Form: White to off-white Solid
Storage : Sealed storage, away from moisture
CAS.NO.: 187794-49-6
CHEMICAl FORMULA: C20H28N4O7
Molar Mass: 436.46
SMILES: CC(C)(C)OC(=O)NCC(=O)NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NCC(=O)O
IUPACNAME: 2-[[(2S)-2-[[2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]acetic acid
INCHIKEY: PTUJJIPXBJJLLV-AWEZNQCLSA-N
INCHI: InChI=1S/C20H28N4O7/c1-20(2,3)31-19(30)23-10-15(25)21-11-16(26)24-14(18(29)22-12-17(27)28)9-13-7-5-4-6-8-13/h4-8,14H,9-12H2,1-3H3,(H,21,25)(H,22,29)(H,23,30)(H,24,26)(H,27,28)/t14-/m0/s1
Application: Boc-Gly-Gly-Phe-Gly-OH is an N- and C-protected tetrapeptide linker designed for antibody-drug conjugate (ADC) research and peptide-based drug delivery applications. This Gly-Gly-Phe-Gly sequence functions as a protease-cleavable linker, enabling enzymatic release of conjugated payloads under specific biological conditions. Its protected structure supports controlled synthesis, conjugation, and incorporation into complex molecular architectures. Boc-Gly-Gly-Phe-Gly-OH is valuable for studying linker stability, payload release mechanisms, and ADC design strategies. It is widely used in medicinal chemistry, chemical biology, peptide synthesis, and targeted therapy research focused on cleavable linker systems and antibody-mediated drug delivery.
Current Research: Boc-Gly-Gly-Phe-Gly-OH is a protected tetrapeptide built from glycine, glycine, phenylalanine, and glycine residues, with an N-terminal Boc protecting group and a C-terminal carboxylic acid. This sequence is of interest in peptide chemistry, linker engineering, self-assembly research, and antibody–drug conjugate development because short peptide linkers can be designed to respond to proteolytic environments while also contributing defined spacing, solubility, and structural behavior to larger molecular constructs. As a protease-cleavable linker, Boc-Gly-Gly-Phe-Gly-OH is used as a modular building block in research workflows involving drug release, bioconjugation, and enzyme-responsive delivery systems. A major application of Boc-Gly-Gly-Phe-Gly-OH is linker design for antibody–drug conjugates, commonly known as ADCs. ADCs typically combine a targeting antibody, a chemical linker, and a cytotoxic payload. The linker is critical because it must remain sufficiently stable during circulation or handling while allowing controlled payload release under intended biological conditions. Protease-cleavable peptide linkers are frequently explored because specific intracellular or tumor-associated proteases can recognize peptide sequences and trigger release after internalization or exposure to disease-associated enzymatic environments. Boc-Gly-Gly-Phe-Gly-OH provides a short, chemically defined peptide segment for investigating protease-sensitive linker behavior. The Gly-Gly-Phe-Gly motif is especially useful for studying how sequence composition affects enzymatic cleavage. Glycine residues provide flexibility, while phenylalanine contributes hydrophobic and aromatic character that may influence protease recognition, self-assembly, and local conformation. In linker design, even small changes in residue order can alter cleavage rate, enzyme preference, solubility, and payload release profile. Researchers may compare Boc-Gly-Gly-Phe-Gly-OH with related sequences such as Gly-Phe-Leu-Gly, Val-Cit, Phe-Lys, Gly-Gly-Phe, or other protease-responsive motifs to determine how structure affects performance. Boc-Gly-Gly-Phe-Gly-OH is also relevant to peptide self-assembly research. N- and C-protected short peptides can form supramolecular structures through hydrogen bonding, hydrophobic interactions, π–π stacking from aromatic residues, and backbone-driven organization. The phenylalanine residue in this tetrapeptide can contribute to aromatic interactions, while the Boc group can increase hydrophobic character and promote ordered assembly under suitable solvent and concentration conditions. Researchers may investigate whether the compound forms nanofibers, gels, aggregates, micellar structures, or other supramolecular architectures. Self-assembling peptide linkers are valuable in drug delivery research because assembly behavior can affect solubility, release kinetics, local concentration, and material properties. Boc-Gly-Gly-Phe-Gly-OH may be studied as a simple model for how protected peptide fragments organize in aqueous or mixed solvent systems. Analytical methods may include transmission electron microscopy, atomic force microscopy, dynamic light scattering, circular dichroism, FTIR, rheology, HPLC, LC-MS, and fluorescence-based aggregation assays. In ADC and bioconjugation research, Boc-Gly-Gly-Phe-Gly-OH may serve as an intermediate rather than the final linker format. The Boc group protects the N-terminus during synthesis, while the C-terminal carboxylic acid can be activated for coupling to amines or incorporated into more complex linker-payload architectures. Researchers may remove the Boc group, extend the peptide, attach spacer units, connect self-immolative groups, or conjugate payloads through amide-forming chemistry. This makes the reagent useful in synthetic route development and linker optimization. Protease-cleavage studies are another important application. A linker candidate can be incubated with purified proteases, lysosomal extracts, tumor cell lysates, serum, or tissue-derived enzyme mixtures to evaluate cleavage sensitivity. Cleavage products can be analyzed by LC-MS, HPLC, fluorescence if a labeled analog is used, or payload release assays in complete conjugates. Such experiments help determine whether the linker is stable in non-target environments and cleavable under intended enzymatic conditions. The compound may also support enzyme-responsive prodrug research. Peptide linkers can be attached to small-molecule payloads, imaging probes, cytotoxic agents, or affinity tags to create constructs that remain masked until proteolytic cleavage occurs. Boc-Gly-Gly-Phe-Gly-OH can be used in early-stage synthesis and model studies evaluating whether Gly-Gly-Phe-Gly-like motifs are suitable for controlled release. In targeted delivery research, linker hydrophobicity and flexibility are important. A linker that is too hydrophobic may promote aggregation of an ADC or peptide–drug conjugate, while a linker that is too flexible or too rapidly cleaved may reduce stability. Boc-Gly-Gly-Phe-Gly-OH provides a compact structure for testing the balance between enzymatic responsiveness, synthetic accessibility, and physicochemical behavior. Experimental controls should include non-cleavable linker analogs, scrambled peptide linkers, related cleavable sequences, enzyme-free controls, heat-inactivated protease controls, serum stability assays, lysosomal extract assays, and LC-MS confirmation of cleavage products. For self-assembly experiments, solvent composition, peptide concentration, pH, ionic strength, temperature, incubation time, and sample aging should be standardized. Overall, Boc-Gly-Gly-Phe-Gly-OH is a versatile protected tetrapeptide linker for chemical biology and drug delivery research. It supports protease-cleavable ADC linker development, peptide–drug conjugate synthesis, self-assembly studies, enzyme-responsive release assays, linker structure–activity optimization, bioconjugation strategy development, and investigation of short protected peptides as functional components in targeted molecular delivery systems.
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