Fmoc-S-4-methoxytrityl-D-cysteine
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Fmoc-S-4-methoxytrityl-D-cysteine

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Fmoc-S-4-methoxytrityl-D-cysteine is used as a reactant in the solid phase synthesis of peptides.

Category
Fmoc-Amino Acids
Catalog number
BAT-007683
CAS number
1198791-73-9
Molecular Formula
C38H33NO5S
Molecular Weight
615.75
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(4-methoxyphenyl)-diphenylmethyl]sulfanylpropanoic acid
Synonyms
Fmoc-D-Cys(Mmt)-OH; Fmoc-D-Cys(4-methoxytrityl)-OH; Fmoc-cys(mmt)-oh; D-Fmoc-Cys(MMt)-OH; N-alpha-(9-Fluorenylmethoxycarbonyl)-S-(4-methoxytrityl)-D-cysteine; (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(4-methoxyphenyl)-diphenylmethyl]sulfanylpropanoic acid
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Storage
Store at 2-8 °C
InChI
InChI=1S/C38H33NO5S/c1-43-29-22-20-28(21-23-29)38(26-12-4-2-5-13-26,27-14-6-3-7-15-27)45-25-35(36(40)41)39-37(42)44-24-34-32-18-10-8-16-30(32)31-17-9-11-19-33(31)34/h2-23,34-35H,24-25H2,1H3,(H,39,42)(H,40,41)/t35-/m1/s1
InChI Key
LOBUWFUSGOYXQX-PGUFJCEWSA-N
Canonical SMILES
COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)SCC(C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46

Fmoc-S-4-methoxytrityl-D-cysteine is a chemical reagent used in peptide synthesis and biochemical research. Here are some key applications of Fmoc-S-4-methoxytrityl-D-cysteine:

Peptide Synthesis: Fmoc-S-4-methoxytrityl-D-cysteine is employed as a protected amino acid in solid-phase peptide synthesis (SPPS). Its Fmoc group protects the amine functionality during synthesis, while the methoxytrityl group protects the thiol functionality of cysteine. This allows for the efficient and selective formation of disulfide bonds in complex peptide structures.

Drug Development: In pharmaceutical research, Fmoc-S-4-methoxytrityl-D-cysteine is used to synthesize peptide-based drugs. These drugs often target specific proteins and enzymes, offering highly selective therapeutic effects. The protected cysteine residue ensures the proper folding and function of the therapeutic peptides, enhancing their stability and efficacy.

Protein Engineering: Fmoc-S-4-methoxytrityl-D-cysteine is utilized in the synthesis of modified proteins and enzymes. By incorporating this protected amino acid, researchers can introduce unique thiol functionalities into proteins. These modified proteins can be used to study protein interactions, enzyme mechanisms, and for creating novel biocatalysts with improved properties.

Bioconjugation: Fmoc-S-4-methoxytrityl-D-cysteine is vital in the development of bioconjugates, where peptides or proteins are linked to other molecules such as drugs, fluorophores, or polymers. The protected cysteine residue allows for selective conjugation through thiol-reactive chemistries. This is crucial for creating targeted drug delivery systems and advanced diagnostic tools.

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