Fmoc-Cys((S)-2,3-di(palmitoyloxy)-propyl)-OH
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Fmoc-Cys((S)-2,3-di(palmitoyloxy)-propyl)-OH

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

SPPS employing the pure stereoisomer of Fmoc-Pam2Cys-OH allows to obtain more homogeneous lipopeptides. The configuration of bis-palmitoyloxypropy moiety can affect the biological activity of peptide conjugation.

Category
Fmoc-Amino Acids
Catalog number
BAT-014633
CAS number
139573-78-7
Molecular Formula
C53H83NO8S
Molecular Weight
894.31
IUPAC Name
(2R)-3-[(2S)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-(S)Pam2Cys-OH; Fmoc-Cys(Pam)2-OH(S); N-alpha-(fluoren-9-ylmethoxycarbonyl)-S-[2,3-bis(palmitoyloxy)-(2R)-propyl]-(R)-cysteine; Hexadecanoic acid, 1,1'-[(1S)-1-[[[(2R)-2-carboxy-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]ethyl]thio]methyl]-1,2-ethanediyl] ester; S-[(2S)-2,3-Bis(palmitoyloxy)propyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cysteine; (2R,6S)-2-(9-Fluorenylmethoxycarbonyl)amino-6,7-bis(palmitoyloxy)-4-thiaheptanic acid
Appearance
White Powder
Purity
≥95%
Density
1.1±0.1 g/cm3
Boiling Point
922.7±65.0°C at 760 mmHg
Storage
Store at -20°C
InChI
InChI=1S/C53H83NO8S/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-37-50(55)60-39-43(62-51(56)38-28-26-24-22-20-18-16-14-12-10-8-6-4-2)41-63-42-49(52(57)58)54-53(59)61-40-48-46-35-31-29-33-44(46)45-34-30-32-36-47(45)48/h29-36,43,48-49H,3-28,37-42H2,1-2H3,(H,54,59)(H,57,58)/t43-,49-/m0/s1
InChI Key
HNJKCVLFJLXANK-UCNLINEOSA-N
Canonical SMILES
CCCCCCCCCCCCCCCC(=O)OCC(CSCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OC(=O)CCCCCCCCCCCCCCC

Fmoc-Cys((S)-2,3-di(palmitoyloxy)propyl)-OH, a synthesized amino acid derivative, finds predominant utility in peptide synthesis and biochemical research. Here are four key applications of Fmoc-Cys((S)-2,3-di(palmitoyloxy)propyl)-OH:

Peptide Synthesis: In the realm of solid-phase peptide synthesis, Fmoc-Cys((S)-2,3-di(palmitoyloxy)propyl)-OH takes center stage, facilitating the incorporation of cysteine residues adorned with lipophilic modifications into peptide chains. This intricate process bestows lipid-like properties upon peptides, enhancing their affinity for membranes and bolstering their membrane-binding capabilities. Such sophisticated modifications play a pivotal role in crafting peptides with heightened systemic delivery potential and heightened membrane interactions.

Protein Engineering: Within the domain of protein engineering, this compound serves as a cornerstone for designing proteins manifesting specific functional traits. By integrating this derivative into their framework, researchers can engender lipidated proteins that mirror the inherent characteristics of naturally occurring lipidated proteins, particularly those implicated in pivotal signaling pathways. This innovative approach enables the exploration of protein-lipid interactions and opens avenues for potential therapeutic interventions, propelling the frontier of protein design.

Bioconjugation Studies: Delving into bioconjugation techniques, Fmoc-Cys((S)-2,3-di(palmitoyloxy)propyl)-OH emerges as a crucial tool for tethering peptides or proteins to lipid bilayers. This sophisticated application lies at the heart of developing liposome-based drug delivery systems and advancing studies on membrane proteins. By anchoring biologically active molecules to cell membranes or synthetic lipid systems, researchers pave the way for comprehensive functional analyses, pushing the boundaries of bioconjugation research to new heights of complexity and impact.

Immunology Research: In the realm of immunology research, this potent molecule finds a niche in formulating lipidated peptide antigens, amplifying the immune response crucial in vaccine development and immune pathway exploration. These tailored peptides, embellished with lipid moieties, serve as potent immune stimulants, enhancing antigen delivery and presentation for heightened efficacy and immunogenicity of vaccines. This intricate lipidation property not only enhances antigenicity but also promises advancements in vaccine design and immune modulation, underscoring the multifaceted role of Fmoc-Cys((S)-2,3-di(palmitoyloxy)propyl)-OH in immunological studies.

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