CAS 270596-48-0

Fmoc-(S)-3-amino-5-hexynoic acid

Description:

Fmoc-(S)-3-amino-5-hexynoic acid is a synthetic amino acid derivative characterized by the presence of a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group, which is commonly used in peptide synthesis to protect the amino group during the coupling reactions. This compound features a chiral center at the 3-position, denoted by the (S) configuration, which contributes to its stereochemical properties. The hexynoic acid moiety includes a terminal alkyne functional group, providing unique reactivity for further chemical modifications, such as click chemistry. The presence of both the amino and alkyne functionalities allows for versatile applications in the synthesis of peptides and other bioactive compounds. Fmoc-(S)-3-amino-5-hexynoic acid is typically used in solid-phase peptide synthesis (SPPS) and can be utilized to introduce specific structural features into peptides, enhancing their biological activity or stability. Its solubility characteristics and stability under standard laboratory conditions make it a valuable building block in organic and medicinal chemistry.

Formula: C₂₁H₁₉NO₄

InChI: InChI=1/C21H19NO4/c1-2-7-14(12-20(23)24)22-21(25)26-13-19-17-10-5-3-8-15(17)16-9-4-6-11-18(16)19/h1,3-6,8-11,14,19H,7,12-13H2,(H,22,25)(H,23,24)/t14-/m0/s1

SMILES: C#CC[C@@H](CC(=O)O)N=C(O)OCC1c2ccccc2c2ccccc12

Synonyms:

• (3S)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hex-5-ynoic acid
• Fmoc-β-HoGly(Propargyl)-OH