139573-77-6

Basic information

• Product Name: Fmoc-Cys(Pam)2-OH (R)
• Synonyms: Fmoc-Cys(Pam)2-OH (R);Hexadecanoic acid (1R)-1-[[[(2R)-2-carboxy-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]ethyl]thio]methyl]-1,2-ethanediyl ester;S-[(2R)-2,3-Bis(palmitoyloxy)propyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cysteine;(9H-Fluoren-9-yl)MethOxy]Carbonyl Cys(Pam)2-OH (R)
• CAS NO: 139573-77-6
• Molecular Formula: C₅₃H₈₃NO₈S
• Molecular Weight: 894.29302
• Mol File: 139573-77-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 922.7±65.0 °C(Predicted)
• Appearance: /
• Density: 1.062±0.06 g/cm3(Predicted)
• PKA: 3.46±0.10(Predicted)
• CAS DataBase Reference: Fmoc-Cys(Pam)2-OH (R)(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-Cys(Pam)2-OH (R)(139573-77-6)
• EPA Substance Registry System: Fmoc-Cys(Pam)2-OH (R)(139573-77-6)

Safety Data

• Hazardous Substances Data: 139573-77-6(Hazardous Substances Data)

Usage

Uses

Fmoc-Cys((R)-2,3-di(palmitoyloxy)-propyl)-OH is a protected L-cysteine (C995000) derivative used in the preparation of synthetic peptides, such as fluorescent Pam3Cys peptide conjugates.

Upstream product

• 57-10-3 1-hexadecylcarboxylic acid 
• 139573-71-0 (R)-tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((R)-2,3-dihydroxypropylthio)propanoate 
• 172322-96-2 (R)-tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-mercaptopropanoate 
• 139592-37-3 (2R,2‘R)-di-tert-butyl 3,3‘-disulfanediylbis(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoate) 
• 139573-75-4 N-fluorenylmethoxycarbonyl-S-[2,3-bis(palmitoyloxy)-(2R)-propyl]-(R)-cysteine tert-butyl ester 

Downstream Products

• 162878-23-1 (S)-2-[4-({[(R)-3-((R)-2,3-Bis-hexadecanoyloxy-propylsulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionyl]-tert-butoxycarbonylmethyl-amino}-methyl)-benzoylamino]-pentanedioic acid di-tert-butyl ester 
• 162878-15-1 (S)-2-(4-{2-[(R)-3-((R)-2,3-Bis-hexadecanoyloxy-propylsulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-acetylamino}-benzoylamino)-pentanedioic acid di-tert-butyl ester 
• 162878-21-9 (S)-2-(4-{[(R)-3-((R)-2,3-Bis-hexadecanoyloxy-propylsulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-methyl}-benzoylamino)-pentanedioic acid di-tert-butyl ester 
• 162878-13-9 (S)-2-{4-[(R)-3-((R)-2,3-Bis-hexadecanoyloxy-propylsulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-benzoylamino}-pentanedioic acid di-tert-butyl ester 

Relevant articles and documents

Design, Synthesis, and Preliminary Immunological Studies of MUC1-Based Antitumor Vaccines Adjuvanted with R- And S-FSL-1

Fibroblast stimulating lipopeptide 1 (FSL-1) is the ligand of TLR2 and TLR6 and can be used as the vaccine adjuvant to prepare antitumor vaccines. However, FSL-1 is a stereoisomeric mixture that contains the R stereoisomer and S stereoisomer, and it is still unclear which stereoisomer has better adjuvant activities. In this work, we designed and synthesized MUC1-based antitumor vaccines adjuvanted with the stereoisomers R-FSL-1 and S-FSL-1, which were synthesized from the stereoisomeric building blocks R-Fmoc-Pam2Cys-OH and S-Fmoc-Pam2Cys-OH, respectively. Immunological evaluation indicated that both R-FSL-1 and S-FSL-1 can be used as adjuvants for the construction of MUC1-based antitumor vaccines, with R-FSL-1 showing a better adjuvant effect than S-FSL-1.

Synthesis and evaluation of fluorescent Pam3Cys peptide conjugates

Chirally pure R- and S-epimers of TLR2 ligand Pam3CysSK4were prepared and separately conjugated to an OVA model epitope, in which lysine was replaced by azidonorleucine. The azide function in the conjugate permitted labelling with di

Stereochemical dependence of the self-assembly of the immunoadjuvants Pam3Cys and Pam3Cys-Ser

The lipopeptide tripalmitoyl-S-glycerylcysteme (Pam3Cys) is derived from the N-terminal part of bacterial lipopeptides and is a polyclonal B-lymphocyte and macrophage activator. Derivatives of Pam3Cys constitute highly potent, nontoxic immunoadjuvants, and lipopeptide - antigen conjugates have found important applications as novel fully synthetic low-molecular-weight vaccines. To establish a possible correlation between molecular structure, aggregation properties, and biological activities, we have studied the self-assembly and monolayer properties of a range of Pam3Cys derivatives using transmission electron microscopy (TEM) and a Langmuir-film balance combined with a Brewster angle microscopy (BAM). It was found that the chirality of the glyceryl moiety and the additional serine unit impacted on the mode of aggregation and the monolayer properties. Correlations are discussed between these physicochemical properties and biological activities.