Fmoc-Cys(Acm)-OPfp
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Fmoc-Cys(Acm)-OPfp

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Category
Fluorinated Amino Acids
Catalog number
BAT-005300
CAS number
86060-96-0
Molecular Formula
C27H21F5N2O5S
Molecular Weight
580.52
Fmoc-Cys(Acm)-OPfp
IUPAC Name
(2,3,4,5,6-pentafluorophenyl) (2R)-3-(acetamidomethylsulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
Synonyms
(2,3,4,5,6-pentafluorophenyl) (2R)-3-(acetamidomethylsulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate; N-Fmoc-S-Acetamidomethyl-L-Cysteine Pentafluorophenyl Ester
Purity
≧ 95%
Density
1.436 g/cm3
Boiling Point
742.4 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C27H21F5N2O5S/c1-13(35)33-12-40-11-19(26(36)39-25-23(31)21(29)20(28)22(30)24(25)32)34-27(37)38-10-18-16-8-4-2-6-14(16)15-7-3-5-9-17(15)18/h2-9,18-19H,10-12H2,1H3,(H,33,35)(H,34,37)/t19-/m0/s1
InChI Key
LTWRDSKMJYQOLL-IBGZPJMESA-N
Canonical SMILES
CC(=O)NCSCC(C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-Cys(Acm)-OPfp is a chemical reagent widely used in peptide synthesis, particularly in the bioscience industry. Here are some key applications of Fmoc-Cys(Acm)-OPfp:

Peptide Synthesis: Fmoc-Cys(Acm)-OPfp is used in solid-phase peptide synthesis to introduce cysteine residues into peptides. Its use allows for the selective protection of cysteine’s thiol group during synthesis. This helps in preventing unwanted side reactions, ensuring the integrity and functionality of the synthesized peptide.

Disulfide Bond Formation: This reagent facilitates the synthesis of peptides that require disulfide bonds, which are critical for the correct folding and stability of peptides and proteins. By protecting the cysteine residues, controlled deprotection and oxidation can be achieved to form precise disulfide linkages. This is essential for producing biologically active peptides with correct structural conformation.

Modification of Biomolecules: Fmoc-Cys(Acm)-OPfp can be used to introduce cys-segments in various biomolecules, which can then be further modified or functionalized. This allows for the addition of labels, conjugates, or other molecular entities, enhancing the properties and applications of the biomolecules. It finds use in creating advanced therapeutic agents and diagnostic tools.

Bioconjugation: In bioconjugation techniques, Fmoc-Cys(Acm)-OPfp is employed to link peptides to other molecules, such as proteins, drugs, or nanoparticles. This enables the creation of complex bioconjugates for targeted drug delivery, diagnostic imaging, or therapeutic purposes. The efficient and selective reactivity of this reagent simplifies the bioconjugation processes, leading to more reliable and reproducible results.

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