Name: Boc-Ser(O-propargyl)-OH
Brand: BOC Sciences
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Synonyms

(S)-2-tert-Butoxycarbonylamino-3-prop-2-ynyloxy-propionic acid

IUPAC Name

(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-prop-2-ynoxypropanoic acid

Canonical SMILES

CC(C)(C)OC(=O)NC(COCC#C)C(=O)O

InChI

InChI=1S/C11H17NO5/c1-5-6-16-7-8(9(13)14)12-10(15)17-11(2,3)4/h1,8H,6-7H2,2-4H3,(H,12,15)(H,13,14)/t8-/m0/s1

InChIKey

NFJGVLNEGPVSTA-QMMMGPOBSA-N

Boc-Ser(O-propargyl)-OH is a propargylated derivative of serine that is used in peptide synthesis and chemical biology research. Here are some key applications of Boc-Ser(O-propargyl)-OH:

Peptide Synthesis: Boc-Ser(O-propargyl)-OH is commonly used in solid-phase peptide synthesis (SPPS) to introduce serine residues with propargyl groups. These propargyl groups provide a handle for further chemical modifications, such as cyclization or conjugation with other molecules. This allows the creation of peptides with unique and diverse functionalities.

Click Chemistry: The propargyl group in Boc-Ser(O-propargyl)-OH is highly compatible with click chemistry reactions, particularly the copper-catalyzed azide-alkyne cycloaddition (CuAAC). This feature facilitates the attachment of various azide-containing compounds to the serine residue, enabling the construction of complex biomolecular assemblies. Such modifications are useful for studying protein interactions, cellular imaging, and drug delivery applications.

Proteomics: In proteomics research, Boc-Ser(O-propargyl)-OH can be used to label and track serine residues within peptides and proteins. The propargyl group can be selectively reacted with tags or probes, aiding in the identification and quantification of serine-containing peptides in complex mixtures. This technique enhances the study of post-translational modifications and protein dynamics.

Phosphorylation Studies: Boc-Ser(O-propargyl)-OH can be utilized in phosphorylation studies to investigate the role of serine phosphorylation in cellular signaling pathways. By incorporating this modified serine into peptides or proteins, researchers can create mimics or inhibitors of phosphorylated serine sites. This helps in understanding the regulatory mechanisms of kinases and phosphatases involved in serine phosphorylation.