Z-S-benzyl-L-cysteine
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Z-S-benzyl-L-cysteine

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Category
CBZ-Amino Acids
Catalog number
BAT-003418
CAS number
3257-18-9
Molecular Formula
C18H19NO4OS
Molecular Weight
345.40
Z-S-benzyl-L-cysteine
IUPAC Name
(2R)-3-benzylsulfanyl-2-(phenylmethoxycarbonylamino)propanoic acid
Synonyms
Z-L-Cys(Bzl)-OH; Z-(S)-2-amino-3-(S-benzylthio)propanoic acid; (R)-2-(((Benzyloxy)carbonyl)amino)-3-(benzylthio)propanoic acid; Cbz-Cys(Bzl)-OH; N-Cbz-S-benzyl-L-cysteine
Appearance
White crystalline powder
Purity
≥ 99% (HPLC)
Density
1.278 g/cm3
Melting Point
86-95 °C
Boiling Point
560.6 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C18H19NO4S/c20-17(21)16(13-24-12-15-9-5-2-6-10-15)19-18(22)23-11-14-7-3-1-4-8-14/h1-10,16H,11-13H2,(H,19,22)(H,20,21)/t16-/m0/s1
InChI Key
ATPNWHGYKFXQNF-INIZCTEOSA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)NC(CSCC2=CC=CC=C2)C(=O)O

Z-S-benzyl-L-cysteine, a synthetic amino acid derivative, finds diverse applications in the field of biosciences. Here are four key applications:

Enzyme Inhibition Studies: Acting as a model compound for investigating enzyme inhibition mechanisms, Z-S-benzyl-L-cysteine is a valuable tool for researchers. It provides insights into the intricate interactions between enzymes and modified amino acid substrates, aiding in the development of enzyme inhibitors for therapeutic purposes and advancing our knowledge of enzyme regulation.

Protein Structure Analysis: In the realm of structural biology, Z-S-benzyl-L-cysteine plays a crucial role in probing protein folding and stability. By substituting natural amino acids with this derivative, scientists can explore changes in protein structure using sophisticated techniques such as X-ray crystallography and NMR spectroscopy. These studies offer glimpses into protein dynamics and potential drug-binding sites.

Peptide Synthesis: A fundamental building block in peptide synthesis, Z-S-benzyl-L-cysteine contributes to the creation of peptides endowed with enhanced stability and functionality. Its incorporation into peptide chains results in molecules that exhibit greater resistance to degradation, with applications spanning drug development and research tools in biochemistry and molecular biology.

Redox Biology Research: Delving into the realms of redox biology, Z-S-benzyl-L-cysteine serves as a key player in unraveling the roles of cysteine residues in oxidative stress and redox signaling. Researchers leverage its properties to examine how modifications to cysteine residues influence protein function and cellular responses to oxidative environments. Such insights are crucial for deciphering diseases associated with oxidative stress and formulating antioxidant strategies that have the potential to reshape therapeutic interventions.

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