Fmoc-L-Cys(Phacm)-OH
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Fmoc-L-Cys(Phacm)-OH

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Category
Fmoc-Amino Acids
Catalog number
BAT-007672
CAS number
159680-21-4
Molecular Formula
C27H26N2O5S
Molecular Weight
490.60
Fmoc-L-Cys(Phacm)-OH
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[[(2-phenylacetyl)amino]methylsulfanyl]propanoic acid
Synonyms
Nα-(9-Fluorenylmethyloxycarbonyl)-S-Phenylacetylaminomethyl)-L-cysteine; (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((2-phenylacetamido)methyl)thio)propanoic acid; N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-S-[(2-phenylacetamido)methyl]-D-cysteine; N-Alpha-(9-fluorenylmethyloxycarbonyl)-s-(phenylacetylaminomethyl)-L-cysteine; (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[[(2-phenylacetyl)amino]methylsulfanyl]propanoic acid
Appearance
White to off-white powder
Purity
≥ 99.5% (Chiral HPLC)
Density
1.315±0.06 g/cm3 (Predicted)
Melting Point
157-159 °C
Boiling Point
782.7±60.0 °C (Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C27H26N2O5S/c30-25(14-18-8-2-1-3-9-18)28-17-35-16-24(26(31)32)29-27(33)34-15-23-21-12-6-4-10-19(21)20-11-5-7-13-22(20)23/h1-13,23-24H,14-17H2,(H,28,30)(H,29,33)(H,31,32)/t24-/m1/s1
InChI Key
UBFAZPXACZPNQB-XMMPIXPASA-N
Canonical SMILES
C1=CC=C(C=C1)CC(=O)NCSCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-L-Cys(Phacm)-OH is a crucial peptide synthesis reagent used in various research and industrial applications. Here are some key applications of Fmoc-L-Cys(Phacm)-OH:

Peptide Synthesis: Fmoc-L-Cys(Phacm)-OH is widely utilized in solid-phase peptide synthesis (SPPS) due to its protection of the thiol group and ease of deprotection. It is vital for creating peptides with free cysteine residues, which are essential for forming disulfide bonds and maintaining proper peptide structure. This reagent ensures the generation of high-purity peptides for research and therapeutic use.

Drug Development: In pharmaceutical research, Fmoc-L-Cys(Phacm)-OH is employed to synthesize peptide-based drug candidates. Cysteine-containing peptides can mimic physiological peptides or serve as inhibitors and activators of various biological processes. Utilizing this reagent allows for the production of prototype drugs with potential therapeutic applications.

Bioconjugation Studies: Fmoc-L-Cys(Phacm)-OH is instrumental in bioconjugation experiments where peptides are attached to other molecules such as proteins, drugs, or fluorescent probes. The protected cysteine residue can be selectively modified once the peptide is synthesized, enabling precise and controlled conjugation reactions. This application is significant for developing advanced diagnostic and therapeutic tools.

Proteomics Research: In proteomics, Fmoc-L-Cys(Phacm)-OH facilitates the synthesis of cysteine-containing peptides used as standards or for studying protein interactions. These peptides are crucial for mass spectrometry-based analysis of protein modifications and structure. The reagent supports the detailed investigation of protein function, post-translational modifications, and protein-protein interactions.

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