Fmoc-S-acetamidomethyl-D-cysteine
Need Assistance?
  • US & Canada:
    +
  • UK: +

Fmoc-S-acetamidomethyl-D-cysteine

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

Category
Fmoc-Amino Acids
Catalog number
BAT-003829
CAS number
168300-88-7
Molecular Formula
C21H22N2O5S
Molecular Weight
414.50
Fmoc-S-acetamidomethyl-D-cysteine
IUPAC Name
(2S)-3-(acetamidomethylsulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-D-Cys(Acm)-OH; FMOC-D-ACETAMIDOMETHYL-L-CYSTEINE; FMOC-S-ACETAMIDOMETHYL-D-CYSTEINE; S-(Acetamidomethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-cysteine; FMOC-D-CYSTEINE(ACM)-OH
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.327 g/cm3
Melting Point
149-155 °C
Boiling Point
714.1 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C21H22N2O5S/c1-13(24)22-12-29-11-19(20(25)26)23-21(27)28-10-18-16-8-4-2-6-14(16)15-7-3-5-9-17(15)18/h2-9,18-19H,10-12H2,1H3,(H,22,24)(H,23,27)(H,25,26)/t19-/m1/s1
InChI Key
CSMYOORPUGPKAP-LJQANCHMSA-N
Canonical SMILES
CC(=O)NCSCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-S-acetamidomethyl-D-cysteine is a protected amino acid derivative used in peptide synthesis and biochemical research. Here are some key applications of Fmoc-S-acetamidomethyl-D-cysteine:

Peptide Synthesis: Fmoc-S-acetamidomethyl-D-cysteine is frequently used in solid-phase peptide synthesis to introduce cysteine residues while preventing unwanted side reactions. The Fmoc group protects the amino group, and the acetamidomethyl group protects the thiol side chain, allowing for selective deprotection and subsequent reactions. This enables the synthesis of complex peptides with high fidelity and yield.

Protein Engineering: Researchers use Fmoc-S-acetamidomethyl-D-cysteine to incorporate cysteine residues into proteins selectively. This allows for site-specific modifications, such as the introduction of fluorescent labels, cross-linkers, or other post-translational modifications. Such modifications are invaluable for studying protein structure, function, and interactions in a controlled manner.

Drug Development: In medicinal chemistry, Fmoc-S-acetamidomethyl-D-cysteine can be used to design and synthesize peptide-based drugs. The modified cysteine residue provides a handle for introducing drug-like properties, improving stability, or facilitating targeted delivery. This is crucial in developing new therapeutic agents with enhanced efficacy and reduced side effects.

Bioconjugation Studies: Fmoc-S-acetamidomethyl-D-cysteine is used in bioconjugation techniques where peptides or proteins are linked to other molecules, such as drugs, polymers, or nanoparticles. The protected cysteine residue allows for selective and precise attachment of these conjugates. This has significant applications in fields like diagnostics, therapeutic delivery, and biomaterials science.

Online Inquiry
Inquiry Basket