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Fmoc-Gly-Gly-Phe-OH

  CAS No.: 160036-44-2   Cat No.: BADC-00972   Purity: >98.0% 4.5  

Fmoc-Gly-Gly-Phe-OH is a peptide-based ADC linker designed for precise antibody conjugation and controlled intracellular drug release, enhancing specificity and efficacy of antibody-drug conjugates.

Fmoc-Gly-Gly-Phe-OH

Structure of 160036-44-2

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Category
ADC Linker
Molecular Formula
C28H27N3O6
Molecular Weight
501.53
Shipping
Room temperature
Storage
Store at -20 °C, keep in dry and avoid sunlight.

* For research and manufacturing use only. We do not sell to patients.

Size Price Stock Quantity
500 mg $298 In stock

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Popular Publications Citing BOC Sciences Products
Synonyms
(((9H-Fluoren-9-yl)methoxy)carbonyl)glycylglycyl-L-phenylalanine; (S)-11-Benzyl-1-(9H-fluoren-9-yl)-3,6,9-trioxo-2-oxa-4,7,10-triazadodecan-12-oic acid
IUPAC Name
(2S)-2-[[2-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]amino]acetyl]amino]-3-phenylpropanoic acid
Canonical SMILES
C1=CC=C(C=C1)CC(C(=O)O)NC(=O)CNC(=O)CNC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
InChI
InChI=1S/C28H27N3O6/c32-25(29-16-26(33)31-24(27(34)35)14-18-8-2-1-3-9-18)15-30-28(36)37-17-23-21-12-6-4-10-19(21)20-11-5-7-13-22(20)23/h1-13,23-24H,14-17H2,(H,29,32)(H,30,36)(H,31,33)(H,34,35)/t24-/m0/s1
InChIKey
UFGUUZVZUIXKQZ-DEOSSOPVSA-N
Density
1.315±0.06 g/cm3 (Predicted)
Solubility
10 mm in DMSO
Shelf Life
-20°C 3 years powder; -80°C 2 years in solvent
Shipping
Room temperature
Storage
Store at -20 °C, keep in dry and avoid sunlight.
Boiling Point
852.2±65.0 °C (Predicted)

Fmoc-Gly-Gly-Phe-OH is a synthetic tripeptide commonly used in peptide synthesis and biochemical research. Here are some key applications of Fmoc-Gly-Gly-Phe-OH:

Peptide Synthesis: Fmoc-Gly-Gly-Phe-OH is a building block in the solid-phase peptide synthesis (SPPS) process. Its Fmoc (9-fluorenylmethyloxycarbonyl) group provides a temporary protective function, allowing for sequential coupling and de-protection cycles. This helps in constructing longer peptide chains with precise amino acid sequences.

Drug Development: Researchers use Fmoc-Gly-Gly-Phe-OH to design and synthesize peptide-based drug candidates. The inclusion of this tripeptide can help enhance the bioavailability and stability of therapeutic peptides. It plays a role in producing peptides which may act as inhibitors or mimetics of natural ligands in various disease models.

Biochemical Assays: Fmoc-Gly-Gly-Phe-OH is often employed in the development of substrates for enzymatic activity assays. By incorporating the tripeptide into substrates for proteases, researchers can study enzyme kinetics and inhibitor efficacy. This is integral in screening potential drug candidates and understanding enzyme specificity.

Protein-Protein Interaction Studies: In molecular biology, Fmoc-Gly-Gly-Phe-OH can be used to investigate protein-protein interactions. It can be incorporated into peptides that mimic protein binding sites, helping in the study of binding affinities and interaction mechanisms. This insight is important for drug discovery and understanding cellular signaling pathways.

What is the primary application of Fmoc-Gly-Gly-Phe-OH in ADC synthesis?

Fmoc-Gly-Gly-Phe-OH is primarily used as a linker component for peptide-based ADC linkers. The dipeptide sequence (Gly-Gly-Phe) serves as a cleavable substrate for enzymes such as cathepsin B. The Fmoc protecting group and the terminal carboxylic acid are essential for solid-phase peptide synthesis, allowing for precise and controlled addition of further amino acids or a cytotoxic payload.

22/9/2017

Could you advise how the Fmoc group in Fmoc-Gly-Gly-Phe-OH facilitates synthesis?

The Fmoc (9-fluorenylmethoxycarbonyl) group in Fmoc-Gly-Gly-Phe-OH is a base-labile protecting group commonly used in solid-phase peptide synthesis. Its purpose is to protect the alpha-amino group of the first amino acid (Glycine) during the coupling steps. It can be easily removed by a mild base, such as piperidine, without affecting the rest of the peptide chain, enabling subsequent amino acid additions.

18/12/2018

We would like to know the significance of the Gly-Gly-Phe sequence in Fmoc-Gly-Gly-Phe-OH.

The Gly-Gly-Phe sequence in Fmoc-Gly-Gly-Phe-OH is a specific peptide sequence that can be recognized and cleaved by proteases. This sequence is designed to be stable in the bloodstream but is susceptible to cleavage by lysosomal enzymes like cathepsin B after the ADC is internalized. This enzymatic cleavage mechanism ensures that the drug is released specifically within the target cell.

12/4/2022

Dear BOC Sciences, what is the function of the terminal carboxylic acid in Fmoc-Gly-Gly-Phe-OH?

The terminal carboxylic acid (-OH) in Fmoc-Gly-Gly-Phe-OH serves as a functional handle for further chemical modifications. It can be activated and coupled to the amino group of another amino acid or to a payload containing a primary amine. This feature makes it a versatile building block for constructing complex peptide linkers for various ADC platforms.

19/8/2019

Good morning! What are the key stability and storage considerations for Fmoc-Gly-Gly-Phe-OH?

Fmoc-Gly-Gly-Phe-OH should be stored at -20°C under desiccated conditions and protected from light. Exposure to moisture should be minimized to prevent premature Fmoc deprotection. Proper aliquoting helps maintain peptide integrity and ensures consistent performance in peptide synthesis or antibody conjugation applications.

12/12/2017

— Dr. Jessica White, Senior Chemist (USA)

Fmoc-Gly-Gly-Phe-OH peptide linker showed high purity and consistent performance in conjugation reactions.

12/4/2022

— Prof. Markus Schmidt, Medicinal Chemist (Germany)

Batch consistency of Fmoc-Gly-Gly-Phe-OH was excellent, ensuring reliable scale-up.

12/12/2017

— Dr. Claire Dubois, ADC Development Scientist (France)

The Fmoc protection strategy maintained integrity during conjugation. Very high quality linker.

19/8/2019

— Mr. Oliver Hughes, R&D Manager (UK)

BOC Sciences delivered Fmoc-Gly-Gly-Phe-OH with complete analytical documentation and on-time delivery.

22/9/2017

— Dr. Lina Berg, Bioconjugation Specialist (Sweden)

Using this peptide linker, we achieved efficient payload attachment and reproducible ADC yields.

— Ms. Hannah Fischer, Research Scientist (Netherlands)

Fmoc-Gly-Gly-Phe-OH improved our workflow efficiency and conjugation reliability.

18/12/2018

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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