Ac-Cys(farnesyl)-OMe contains a cysteine-derived amino acid derivative in which the thiol side chain is substituted with a farnesyl group and the α-amino functionality is acetylated (Ac), while the carboxyl group is present as a methyl ester (OMe). The molecule bears a thioether-linked farnesyl substituent that increases hydrophobic character and provides a lipid-like handle, with the acetyl and ester groups masking the free amino and carboxyl functionalities to control chemoselectivity during synthesis or conjugation. Ac-Cys(farnesyl)-OMe is used as a chemically defined intermediate or building block for preparing thioether/farnesyl-containing cysteine analogues, supporting structure-activity studies, and enabling analytical or bioconjugation workflows that require a protected, esterified amino acid framework bearing a hydrophobic isoprenoid substituent.
CAT No: CP26329
CAS No:135304-08-4
Synonyms/Alias:135304-08-4;Ac-Cys(farnesyl)-OMe;AC-CYS-OME;C21H35NO3S;ZINC3874352;3909AD;FT-0679808;N-Acetyl-S-farnesyl-L-cysteinemethylester;methyl(2R)-2-acetamido-3-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}propanoate
Ac-Cys(farnesyl)-OMe is an N-acetylated, O-methyl protected cysteine derivative bearing a farnesyl thioether side chain. This structure combines a thioether-functionalized hydrophobic isoprenoid group with protected amine and carboxylate functionalities, making it a compact, lipid-like building block for thioether-containing peptide and conjugate workflows. Researchers use this reagent when a controlled cysteine-farnesyl motif is required without introducing free thiol or unprotected termini.
1. Farnesylated Peptide Building Block
Ac-Cys(farnesyl)-OMe is used as a defined, pre-functionalized cysteine surrogate for assembling peptides and peptide segments that require a farnesylated side chain. In custom peptide synthesis and medicinal chemistry programs, the reagent helps standardize the hydrophobic farnesyl motif while keeping the α-amino and carboxyl groups protected, supporting downstream coupling strategies used to generate thioether-linked lipidated peptide constructs. This format is particularly useful when the target sequence needs a cysteine bearing a farnesyl substituent as a structural element for studying lipid-peptide interactions, membrane association behavior in model systems, or structure-activity relationship trends across analog series.
2. Lipid-Mimetic Bioconjugation Reagents
Ac-Cys(farnesyl)-OMe is applied in chemical biology and biomaterials research to generate lipid-mimetic conjugates where a farnesylated cysteine motif is incorporated into larger constructs. The reagent's protected backbone minimizes side reactions from free amine or carboxylate groups during conjugation development, while the farnesyl thioether provides a hydrophobic handle that can drive partitioning into lipid environments or improve compatibility with amphiphilic assemblies. Teams developing farnesylated peptide probes, surface-associated ligands, or hydrophobic conjugate scaffolds commonly rely on such building blocks to reproduce the same lipid motif across multiple experimental batches.
3. Hydrophobic Motif Standards
Ac-Cys(farnesyl)-OMe is frequently used as a reference material for analytical method development and characterization of farnesylated peptide or conjugate products. In LC-MS workflows, synthetic chemists and analytical scientists use well-defined lipidated amino acid derivatives to confirm retention behavior, fragmentation patterns, and identity of farnesyl-containing intermediates or final conjugates. The N-acetyl and O-methyl protection pattern also supports consistent handling and comparison when quantifying or verifying series of analogs that differ in sequence context but share the same farnesylated cysteine unit.
4. Farnesylated Intermediate Development
Ac-Cys(farnesyl)-OMe serves as a practical intermediate for constructing larger thioether-containing molecules in pharmaceutical intermediate development and peptide-derivative manufacturing research. Process and R&D groups use the reagent to introduce the farnesylated cysteine motif early in a synthetic sequence, enabling controlled elaboration into higher-molecular-weight intermediates used for library synthesis or structure optimization. By maintaining protected termini, the building block supports selective downstream transformations and reduces variability associated with handling free functional groups, which is valuable when preparing multiple analogs that must retain the same lipid substitution pattern.
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