S-Trityl-D-cysteine methyl ester hydrochloride
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S-Trityl-D-cysteine methyl ester hydrochloride

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Category
D-Amino Acids
Catalog number
BAT-001583
CAS number
1020369-32-7
Molecular Formula
C23H24ClNO2S
Molecular Weight
413.97
IUPAC Name
methyl (2S)-2-amino-3-tritylsulfanylpropanoate;hydrochloride
Synonyms
H-D-Cys(Trt)-OMe HCl
InChI
InChI=1S/C23H23NO2S.ClH/c1-26-22(25)21(24)17-27-23(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20;/h2-16,21H,17,24H2,1H3;1H/t21-;/m1./s1
InChI Key
BBLIVDURNAQWLB-ZMBIFBSDSA-N
Canonical SMILES
COC(=O)C(CSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)N.Cl

S-Trityl-D-cysteine methyl ester hydrochloride, a potent chemical compound, finds applications in biochemistry and pharmaceutical research. Here are four key applications:

Enzyme Inhibition Studies: Serving as a formidable inhibitor in enzyme studies, S-Trityl-D-cysteine methyl ester hydrochloride plays a pivotal role in probing the functions of cysteine proteases. By impeding these enzymes’ activities, researchers unlock insights into their involvements in diverse biological pathways and disease mechanisms. This knowledge lays the groundwork for crafting precise enzyme inhibitors tailored for therapeutic interventions.

Structural Biology: Valued in the realm of structural biology, this compound facilitates the examination of proteins’ three-dimensional configurations, especially those featuring cysteine residues. Through the formation of stable adducts with cysteine residues, crystallographers gain a clearer understanding of protein structures, aiding in rational drug design and the creation of novel therapeutic agents with greater precision.

Drug Discovery: Within pharmaceutical research, S-Trityl-D-cysteine methyl ester hydrochloride acts as a foundational compound for designing next-generation drugs targeting cysteine interactions. By scrutinizing its interactions with cysteine residues in target proteins, chemists refine derivatives to boost efficacy and specificity. This strategy streamlines the development of innovative drugs, boasting superior therapeutic benefits.

Proteomic Analysis: In the realm of proteomics, S-Trityl-D-cysteine methyl ester hydrochloride enables the selective modification and labeling of cysteine-containing peptides and proteins, aiding in their identification and characterization using advanced analytical methods like mass spectrometry. These modifications unlock crucial insights into protein functionality, post-translational modifications, and intricate protein-protein interactions, advancing our understanding of cellular processes.

2. An efficient enantioselective synthesis of ( S)-α-methyl-serine methyl ester hydrochloride via asymmetrically catalyzed amination
Qiong Xiao, Yi-Fan Tang, Ping Xie J Asian Nat Prod Res. 2020 Jan;22(1):61-68. doi: 10.1080/10286020.2019.1634058. Epub 2019 Jul 16.
We present the synthesis of enantiomerically pure (S)-α-methyl-serine methyl ester hydrochloride from 2-methyl-3-((4-(trifluoromethyl)benzyl)oxy)propanal and di-p-chlorobenzyl azodicarboxylate via asymmetrically catalyzed amination with naphthylalanine derivative catalyst. The application of the organocatalyst of D-3-(1-Naphthyl)-alanine is the key step in the synthesis and ensures the product is obtained with high levels of stereocontrol.
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