Fmoc-Gly-Gly-Phe-OtBu
[CAS# 236426-37-2]

Identification

• Classification: Biochemical >> Peptide
• Name: Fmoc-Gly-Gly-Phe-OtBu
• Synonyms: tert-butyl (2S)-2-[[2-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]amino]acetyl]amino]-3-phenylpropanoate
• Protein Sequence: GGF
• Molecular Formula: C₃₂H₃₅N₃O₆
• Molecular Weight: 557.64
• CAS Registry Number: 236426-37-2
• SMILES: CC(C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.585, Calc.^*
• Boiling Point: 806.7±65.0 ºC (760 mmHg), Calc.^*
• Flash Point: 441.7±34.3 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovory and Applicatios

Fmoc-Gly-Gly-Phe-OtBu is a protected tripeptide commonly used in peptide synthesis and biochemical research. It consists of three amino acid residues: glycine (Gly), glycine (Gly), and phenylalanine (Phe), with N-terminal protection by the 9-fluorenylmethoxycarbonyl (Fmoc) group and C-terminal protection by the tert-butyl (OtBu) ester. These protecting groups are essential in solid-phase peptide synthesis (SPPS), where they facilitate sequential amino acid coupling and prevent unwanted side reactions.

The development of Fmoc-based peptide synthesis traces back to the introduction of the Fmoc protecting group in the 1970s as an alternative to the Boc (tert-butyloxycarbonyl) strategy. The Fmoc method gained popularity due to its compatibility with mild deprotection conditions using piperidine, which minimizes side reactions and is suitable for automated peptide synthesis. The incorporation of Fmoc-Gly-Gly-Phe-OtBu into peptide synthesis aligns with the broader advancements in synthetic strategies that have enabled the efficient production of peptides for pharmaceutical and biochemical applications.

Fmoc-Gly-Gly-Phe-OtBu is primarily used as an intermediate in the synthesis of peptides and peptide-based drugs. The presence of glycine residues in the sequence provides flexibility to the peptide backbone, while the phenylalanine residue contributes to hydrophobic interactions and potential aromatic stacking. These properties make this tripeptide useful in designing biologically active peptides, particularly those involved in enzyme inhibition, receptor binding, or structural studies.

One significant application of Fmoc-Gly-Gly-Phe-OtBu is in the synthesis of peptide-based biomaterials and drug delivery systems. Peptides containing glycine and phenylalanine sequences are often studied for their self-assembling properties, which are relevant to the development of nanomaterials and hydrogels for biomedical applications. The ability of peptides to form stable secondary structures, such as β-sheets and fibrillar assemblies, is an important aspect of their functional properties in material science.

In addition, Fmoc-Gly-Gly-Phe-OtBu is useful in the study of enzyme-substrate interactions and protease specificity. Short peptide sequences containing glycine and phenylalanine are often used as model substrates for enzymatic cleavage studies, particularly in the investigation of proteolytic pathways and the development of enzyme inhibitors.

The use of Fmoc-Gly-Gly-Phe-OtBu in peptide synthesis continues to support advancements in medicinal chemistry, biomaterials, and protein engineering. Its role as a protected tripeptide intermediate highlights its importance in the development of synthetic peptides for therapeutic and research applications.

References

(2016). Anti-her2 antibody-drug conjugate. US-2016333112-A1, 2016-11-17.
Priority Date: 2014-01-31.

(2019). Antibody-drug conjugate. US-10195288-B2, 2019-02-05.
Priority Date: 2012-10-11.

(2020). Method of treating cancer comprising administration of anti-her2 antibody-drug conjugate. US-2020385486-A1, 2020-12-10.
Priority Date: 2014-01-31.