Nα-Fmoc-S-Palmitoyl-L-cysteine
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Nα-Fmoc-S-Palmitoyl-L-cysteine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007742
CAS number
824955-27-3
Molecular Formula
C34H47NO5S
Molecular Weight
581.80
Nα-Fmoc-S-Palmitoyl-L-cysteine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hexadecanoylsulfanylpropanoic acid
Synonyms
Fmoc-L-Cys(Palm)-OH; Fmoc-l-cys(palm)-oh; Fmoc-Cys(Palo)-OH; Fmoc-S-Palmitoyl-Cys-OH; N-alpha-(9-Fluorenylmethoxycarbonyl)-S-palmitoyl-L-cysteine; L-Cysteine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, hexadecanoate(ester); (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hexadecanoylsulfanylpropanoic acid
Appearance
White crystalline powder
Purity
≥ 99% (HPLC, TLC)
Density
1.123±0.06 g/cm3 (Predicted)
Melting Point
90-92 °C
Boiling Point
720.1±60.0 °C (Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C34H47NO5S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-23-32(36)41-25-31(33(37)38)35-34(39)40-24-30-28-21-17-15-19-26(28)27-20-16-18-22-29(27)30/h15-22,30-31H,2-14,23-25H2,1H3,(H,35,39)(H,37,38)/t31-/m0/s1
InChI Key
LIVQOYPTIAPEAG-HKBQPEDESA-N
Canonical SMILES
CCCCCCCCCCCCCCCC(=O)SCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Nα-Fmoc-S-Palmitoyl-L-cysteine, an amino acid derivative with specialized applications in biochemical and pharmaceutical research, is widely utilized across diverse domains.

Peptide Synthesis: Diving into solid-phase peptide synthesis, Nα-Fmoc-S-Palmitoyl-L-cysteine plays a pivotal role in seamlessly inserting palmitoylated cysteine residues into peptide chains. This crucial modification is indispensable for delving into protein acylation and its profound repercussions on protein structure and function. Palmitoylation, a multifaceted process influencing protein-membrane interactions, stability, and intracellular signaling, injects layers of intricacy into peptide studies.

Drug Delivery: Within lipid-based drug delivery systems, this compound stands as a cornerstone, augmenting hydrophobicity and membrane permeability by attaching palmitoyl groups to therapeutic peptides or proteins. This conjugation elevates drug bioavailability and stability, amplifying their effectiveness in reaching target cells or tissues. The nuances of drug delivery mechanisms are further enriched through this modification.

Functional Studies of Protein Palmitoylation: Harnessing Nα-Fmoc-S-Palmitoyl-L-cysteine, researchers construct intricate model systems to unravel the complex realm of protein palmitoylation, a post-translational modification pivotal for protein trafficking and signaling. By integrating this palmitoylated cysteine into synthetic peptides or recombinant proteins, scientists decipher the functions and cellular pathways steered by palmitoylation. This comprehensive exploration illuminates the role of palmitoylation in diverse biological processes and disease conditions, adding layers of sophistication to our comprehension of protein regulation.

Bioconjugation: The intrinsic palmitoyl group within Nα-Fmoc-S-Palmitoyl-L-cysteine emerges as a potent instrument for modifying biomolecules like antibodies or enzymes, transforming their hydrophobic properties and interactions. This revolutionary technique plays a crucial role in crafting stable bioconjugates for diagnostics, therapeutics, and biochemical studies. The enhanced solubility, stability, and binding characteristics of the modified biomolecules introduce a novel dimension of complexity to bioconjugation methodologies, paving the path for groundbreaking advancements in biochemistry.

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