Boc-Cys(SEt)-OH · DCHA
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Boc-Cys(SEt)-OH · DCHA

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Category
BOC-Amino Acids
Catalog number
BAT-015424
CAS number
25461-01-2
Molecular Formula
C10H19NO4S2 · C12H23N
Molecular Weight
462.72
Boc-Cys(SEt)-OH · DCHA
IUPAC Name
N-cyclohexylcyclohexanamine;(2R)-3-ethylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-L-Cys(Et)-OH DCHA; DIcyclohexylamine (R)-2-((tert-butoxycarbonyl)amino)-3-(ethylthio)propanoate
Appearance
White Powder
Purity
99%
Density
1.229±0.06 g/cm3
Boiling Point
426.4±40.0 °C at 760 mmHg
InChI
InChI=1S/C12H23N.C10H19NO4S/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;1-5-16-6-7(8(12)13)11-9(14)15-10(2,3)4/h11-13H,1-10H2;7H,5-6H2,1-4H3,(H,11,14)(H,12,13)/t;7-/m.0/s1
InChI Key
ZZLHNCHMISOWHS-ZLTKDMPESA-N
Canonical SMILES
CCSCC(C(=O)O)NC(=O)OC(C)(C)C.C1CCC(CC1)NC2CCCCC2

Boc-Cys(SEt)-OH · DCHA, a shielded form of cysteine, is a crucial component in peptide synthesis and diverse biochemical applications. Here are four critical applications:

Peptide Synthesis: At the core of solid-phase peptide synthesis lies the incorporation of Boc-Cys(SEt)-OH · DCHA as a foundational unit, facilitating the construction of peptides with meticulous sequences. The Boc group shields the amino group of cysteine, while the SEt group protects the thiol group, thwarting unwanted side reactions. Post-peptide assembly, these protective entities can be eliminated, unveiling the final functional peptide ripe for biological interactions.

Bioconjugation Studies: Delving into the realm of bioconjugation research, Boc-Cys(SEt)-OH · DCHA emerges as a pivotal player, binding peptides to an array of molecules, from drugs to probes to proteins. Selective deprotection of the shielded thiol group paves the way for reactions with maleimides and other thiol-reactive agents, forming enduring thioether bonds. This application stands as a cornerstone in crafting targeted therapeutics and cutting-edge diagnostic tools.

Structure-Activity Relationship (SAR) Studies: Scientists turn to Boc-Cys(SEt)-OH · DCHA in delving into structure-activity relationship studies, deciphering the intricate roles of cysteine residues in the functionality of proteins and peptides. By synthesizing analogs, with and sans the cysteine residue, researchers unlock insights into its impact on biological activity, pivotal for the meticulous design of drugs and the fine-tuning of proteins for diverse applications.

Protease Inhibitor Development: Pioneering the frontier of cysteine-based protease inhibitors lies Boc-Cys(SEt)-OH · DCHA, integrated into peptide sequences to mimic the target proteases’ substrates. This strategic design enables the creation of inhibitors capable of thwarting enzyme activity with precision. The application bears profound implications for combatting diseases driven by dysregulated protease activity, ranging from cancer to infectious ailments, heralding new avenues for therapeutic interventions.

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