Fmoc-S-4-methyltrityl-D-cysteine
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Fmoc-S-4-methyltrityl-D-cysteine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007684
CAS number
252206-29-4
Molecular Formula
C38H33NO4S
Molecular Weight
599.75
Fmoc-S-4-methyltrityl-D-cysteine
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(4-methylphenyl)-diphenylmethyl]sulfanylpropanoic acid
Synonyms
Fmoc-D-Cys(Mtt)-OH; N-Fmoc-S-[(4-methylphenyl)diphenylmethyl]-D-cysteine; N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-S-[(4-methylphenyl)(diphenyl)methyl]-L-cysteine; (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-((diphenyl(p-tolyl)methyl)thio)propanoic acid; (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(4-methylphenyl)-diphenylmethyl]sulfanylpropanoic acid
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Storage
Store at 2-8 °C
InChI
InChI=1S/C38H33NO4S/c1-26-20-22-29(23-21-26)38(27-12-4-2-5-13-27,28-14-6-3-7-15-28)44-25-35(36(40)41)39-37(42)43-24-34-32-18-10-8-16-30(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
PCCZXLMDPCBTSL-PGUFJCEWSA-N
Canonical SMILES
CC1=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-methyltrityl-D-cysteine, a derivative of protected amino acid, finds widespread application in peptide synthesis.

Peptide Synthesis: A cornerstone of solid-phase peptide synthesis (SPPS), Fmoc-S-4-methyltrityl-D-cysteine plays a pivotal role in integrating cysteine residues into peptide chains while safeguarding the thiol group. This strategy allows for the creation of peptides harboring free cysteines capable of forming vital disulfide bonds, crucial for upholding the structural integrity of bioactive peptides and proteins. Its employment guarantees the production of peptides with exceptional purity and yield.

Protein Engineering: Within the realm of protein engineering, Fmoc-S-4-methyltrityl-D-cysteine is harnessed to engineer proteins exhibiting specific attributes. By inserting protected cysteine residues, researchers can regulate the formation of disulfide bonds, influencing protein folding, stability, and functionality. This technique proves particularly valuable in crafting therapeutic proteins and enzymes endowed with enhanced performance capabilities.

Chemical Ligation: Embraced in native chemical ligation methods, Fmoc-S-4-methyltrityl-D-cysteine facilitates the merging of peptide fragments. The protective cysteine feature allows for targeted deprotection and activation, facilitating the fusion of two segments through peptide bond formation. This methodology serves as a linchpin for constructing intricate and sizable peptide and protein architectures.

Drug Design and Development: In the sphere of drug discovery, Fmoc-S-4-methyltrityl-D-cysteine emerges as a key player in the creation of peptide-based drug candidates. By incorporating this amino acid, scientists can engineer peptides endowed with enhanced pharmacokinetic and pharmacodynamic properties, such as heightened stability and specificity towards target molecules. Its utilization is instrumental in molding peptide therapeutics tailored to address diverse medical conditions.

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