N-acetyl-S-trans,trans-farnesyl-L-cysteine, CAS No. 135304-07-3

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135304-07-3

Catalog No. EBD266420

CAS 135304-07-3

Name N-acetyl-S-trans,trans-farnesyl-L-cysteine

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Basic Information

Synonyms: N-acetyl-S-trans,trans-farnesyl-L-cysteine N-acetyl-S-farnesyl-L-cysteine N-acetylcystein(S-farnesyl) (R)-2-acetamido-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoicacid N-acetyl-S-farnesyl-L-Cys AFC Ac-Cys(farnesyl)-OH N-acetyl-S-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-L-cysteine Arazine L-Cysteine,N-acetyl-S-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]- ac-cysteine(farnesyl)-oh acetyl-s-farnesyl-l-cysteine n-acetyl-s-(3,7,11-trimethyl-2e,6e,10-dodecatrienyl)-l-cysteine n-alpha-acetyl-s-farnesyl-l-cysteine n-acetyl-s-farnesylcysteine

Molecular Formula: C20H33NO3S

Molecular Weight: 367.55

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Lipids and Derivatives Medicinal Chemistry > Pharmaceutical Intermediates > Other Pharmaceutical Intermediates

Product Description:

N-Acetyl-S-farnesyl-L-cysteine (AFC) is a synthetic, prenylated cysteine derivative. It is structurally characterized by the conjugation of an N-acetyl-L-cysteine moiety with a 15-carbon farnesyl isoprenoid chain via a thioether linkage. This structure mimics the C-terminal motif of prenylated proteins, particularly those modified by farnesyltransferase. Its primary application is in biochemical and pharmacological research as a specific, cell-permeable inhibitor of farnesyltransferase. AFC acts as a competitive inhibitor by mimicking the C-terminal CAAX motif of substrate proteins, thereby blocking the transfer of the farnesyl group from farnesyl pyrophosphate to target proteins like Ras. This mechanism has made it a valuable tool for studying the role of protein prenylation in cell signaling, proliferation, and oncogenesis. It is used to investigate diseases associated with aberrant Ras signaling. While not a therapeutic agent itself, AFC serves as a crucial research chemical and a potential lead compound or intermediate in the development of farnesyltransferase inhibitors (FTIs) for cancer therapy. Its use is confined to laboratory research settings.

Physical Properties

Boiling Point: 566.1 °C at 760 mmHg

Flash Point: 296.1 °C

Density: 1.038 g/cm3