Name: Fmoc-Gly-Gly-Phe-OtBu
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

tert-butyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]glycylglycyl-L-phenyl alaninate; tert-butyl (2S)-2-[[2-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]amino]acetyl]amino]-3-phenylpropanoate

IUPAC Name

tert-butyl (2S)-2-[[2-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]amino]acetyl]amino]-3-phenylpropanoate

Canonical SMILES

CC(C)(C)OC(=O)C(CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

InChI

InChI=1S/C32H35N3O6/c1-32(2,3)41-30(38)27(17-21-11-5-4-6-12-21)35-29(37)19-33-28(36)18-34-31(39)40-20-26-24-15-9-7-13-22(24)23-14-8-10-16-25(23)26/h4-16,26-27H,17-20H2,1-3H3,(H,33,36)(H,34,39)(H,35,37)/t27-/m0/s1

InChIKey

XQLGBXCTOOARCT-MHZLTWQESA-N

Solubility

10 mm in DMSO

Appearance

Solid

Shelf Life

0-4°C for short term (days to weeks), or -20°C for long term (months).

Shipping

Room temperature, or blue ice upon request.

Storage

Store at -20 °C, keep in dry and avoid sunlight.

Form

Solid

Biological Activity

Fmoc-Gly-Gly-Phe-OtBu is a cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs)[1]

Fmoc-Gly-Gly-Phe-OtBu is a peptide compound commonly used in the field of peptide synthesis. It serves as an important building block in the solid-phase peptide synthesis (SPPS) method, where it is utilized to form longer peptide chains. The Fmoc (9-fluorenylmethyloxycarbonyl) group is particularly useful as a temporary protecting group for the amino terminus of the peptide during synthesis. The Fmoc group is easily removed under mildly basic conditions, which allows for sequential addition of amino acids while minimizing side reactions. This functionality makes Fmoc-Gly-Gly-Phe-OtBu a versatile intermediate for complex peptide assembly.

Additionally, Fmoc-Gly-Gly-Phe-OtBu is employed in the development of bioactive peptides for therapeutic applications. The presence of phenylalanine (Phe) in the sequence provides aromaticity, which is essential for certain receptor interactions or to impart specific structural properties to the resulting peptides. This can be crucial in the development of peptides that target proteins or receptors involved in disease mechanisms. Moreover, the glycine residues (Gly-Gly) may contribute to flexibility in the peptide structure, facilitating its interaction with other biomolecules.

The OtBu (tert-butoxy) group, which protects the carboxyl group during synthesis, is another significant feature of Fmoc-Gly-Gly-Phe-OtBu. This protective group helps maintain stability during the synthesis process and can be removed selectively when needed. The OtBu group also contributes to the compound's overall stability, preventing premature cleavage or reactions that could compromise the integrity of the peptide chain. This makes Fmoc-Gly-Gly-Phe-OtBu an ideal candidate for use in controlled synthesis protocols, where maintaining precise structural integrity is essential.

In addition to its application in peptide synthesis, Fmoc-Gly-Gly-Phe-OtBu is valuable in studies of protein folding and interaction. The specific arrangement of amino acids within this compound can be tailored to mimic certain structural motifs found in proteins, making it a useful tool in structural biology. By incorporating such compounds into experimental models, researchers can gain insights into the principles of peptide folding, stability, and the mechanisms by which peptides interact with their biological targets.