Name: Fmoc-L-Dap(Pentynoyl)-OH
Brand: BOC Sciences
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IUPAC Name

(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(pent-4-ynoylamino)propanoic acid

Canonical SMILES

C#CCCC(=O)NCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

InChI

InChI=1S/C23H22N2O5/c1-2-3-12-21(26)24-13-20(22(27)28)25-23(29)30-14-19-17-10-6-4-8-15(17)16-9-5-7-11-18(16)19/h1,4-11,19-20H,3,12-14H2,(H,24,26)(H,25,29)(H,27,28)/t20-/m0/s1

InChIKey

GPEIHIDRFBLIMO-FQEVSTJZSA-N

Fmoc-L-Dap(Pentynoyl)-OH, a specialized amino acid derivative, plays a pivotal role in peptide synthesis and diverse bioscience applications. Here are four key applications:

Peptide Synthesis: Integral to solid-phase peptide synthesis, Fmoc-L-Dap(Pentynoyl)-OH enables the stepwise assembly of peptides, crucial for drug development and biochemical investigations. The Fmoc protective group allows for precise peptide construction devoid of unwanted side reactions. This compound empowers the creation of peptides with tailored functionalities, like integrating alkyne moieties for subsequent bio-orthogonal reactions.

Bio-orthogonal Chemistry: Researchers harness Fmoc-L-Dap(Pentynoyl)-OH to introduce alkyne groups into peptides, facilitating bio-orthogonal click chemistry reactions. These biocompatible reactions are indispensable for labeling and modifying biomolecules in intricate biological settings. This application plays a pivotal role in probing protein interactions, monitoring cellular dynamics, and designing targeted drug delivery systems.

Structural Biology: In the realm of structural biology, Fmoc-L-Dap(Pentynoyl)-OH aids in crafting peptides with distinctive structural attributes, enhancing the study of protein folding and conformational dynamics. By incorporating this amino acid derivative into peptide sequences, researchers can induce specific interactions and stabilize particular peptide conformations. This advancement furthers our comprehension of protein function at a structural level, aiding in the development of peptide-based therapeutics.

Chemical Biology Tools: Serving as a foundational component in the development of chemical biology tools and probes, Fmoc-L-Dap(Pentynoyl)-OH assists in exploring biological pathways, identifying enzyme activities, and mapping out cellular processes. The pentynoyl group offers a versatile platform for click chemistry, enabling the creation of multifunctional biomolecular conjugates essential for advancing research in chemical biology.