Boc-S-trityl-L-cysteine
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Boc-S-trityl-L-cysteine

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Category
BOC-Amino Acids
Catalog number
BAT-002901
CAS number
21947-98-8
Molecular Formula
C27H29NO4S
Molecular Weight
463.57
Boc-S-trityl-L-cysteine
IUPAC Name
(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-tritylsulfanylpropanoic acid
Synonyms
Boc-L-Cys(Trt)-OH; (R)-2-tert-Butoxycarbonylamino-3-tritylsulfanyl-propionic acid; N-(tert-Butoxycarbonyl)-S-trityl-L-cysteine
Appearance
White to off-white powder
Purity
≥ 99.5% (Chiral HPLC)
Density
1.200±0.06 g/cm3(Predicted)
Melting Point
142-150 °C
Boiling Point
610.9±55.0 °C(Predicted)
Storage
Store at 2-8°C
InChI
InChI=1S/C27H29NO4S/c1-26(2,3)32-25(31)28-23(24(29)30)19-33-27(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22/h4-18,23H,19H2,1-3H3,(H,28,31)(H,29,30)/t23-/m0/s1
InChI Key
JDTOWOURWBDELG-QHCPKHFHSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)O

Boc-S-trityl-L-cysteine, a versatile protected amino acid derivative, finds extensive use in peptide synthesis and biochemical research. Here are four key applications of Boc-S-trityl-L-cysteine:

Peptide Synthesis: Playing a fundamental role in solid-phase peptide synthesis (SPPS), Boc-S-trityl-L-cysteine incorporates a Boc protecting group that safeguards the integrity of the cysteine residue throughout peptide elongation. This meticulous preservation is indispensable for crafting peptides with intricate sequences and tailored functionalities, pushing the boundaries of peptide chemistry.

Disulfide Bond Formation Studies: Within the realm of disulfide bond formation and protein folding investigations, Boc-S-trityl-L-cysteine takes center stage. By integrating it into peptide chains, researchers embark on unraveling the intricate mechanisms underlying how disulfide bonds influence the structure and stability of proteins. This exploration holds particular significance in deciphering the folding intricacies of proteins rich in cysteine residues, shedding light on their structural nuances.

Protecting Group Chemistry: In the domain of protecting group chemistry research, Boc-S-trityl-L-cysteine emerges as a pivotal player, elucidating the dynamics of protecting group stability and removal in organic synthesis. The trityl group delivers robust protection while offering facile removal under mild acidic conditions, a characteristic crucial for synthetic routes necessitating selective deprotection. This utility empowers researchers to navigate intricate synthetic pathways with precision and finesse, advancing the field of organic chemistry.

Bioconjugation: Facilitating bioconjugation endeavors, Boc-S-trityl-L-cysteine enables the attachment of diverse biomolecules to peptides or proteins through its reactive cysteine thiol group post-deprotection. This feature permits site-specific conjugation with small molecules, fluorophores, or other proteinaceous materials, catalyzing the development of biopharmaceuticals and diagnostic tools. The strategic application of Boc-S-trityl-L-cysteine in bioconjugation endeavors underscores its pivotal role in expanding the horizons of biomedical research and therapeutic innovation.

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