S-Benzyl-L-cysteine
Need Assistance?
  • US & Canada:
    +
  • UK: +

S-Benzyl-L-cysteine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category
L-Amino Acids
Catalog number
BAT-004193
CAS number
3054-01-1
Molecular Formula
C10H13NO2S
Molecular Weight
211.30
S-Benzyl-L-cysteine
IUPAC Name
(2R)-2-amino-3-benzylsulfanylpropanoic acid
Synonyms
L-Cys(Bzl)-OH; (R)-2-Amino-3-benzylsulfanyl-propionic acid
Appearance
White to off-white crystalline powder
Purity
≥ 98%
Density
1.22 g/cm3
Melting Point
208-214 °C
Boiling Point
350.9°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C10H13NO2S/c11-9(10(12)13)7-14-6-8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)/t9-/m0/s1
InChI Key
GHBAYRBVXCRIHT-VIFPVBQESA-N
Canonical SMILES
C1=CC=C(C=C1)CSCC(C(=O)O)N

S-Benzyl-L-cysteine is a versatile compound used in various scientific and industrial applications. Here are some key applications of S-Benzyl-L-cysteine:

Pharmaceutical Research: S-Benzyl-L-cysteine is utilized as a precursor in the synthesis of various medicinal compounds. Its unique structure makes it an important building block for drugs aimed at treating conditions like hypertension and chronic obstructive pulmonary disease (COPD). Research on S-Benzyl-L-cysteine can lead to the development of novel therapeutic agents with improved efficacy and safety profiles.

Chemical Synthesis: S-Benzyl-L-cysteine is a valuable intermediate in organic synthesis, particularly in the production of amino acids, peptides, and other bioactive molecules. Its benzyl group can be selectively removed or modified, allowing chemists to create complex molecules for research and industrial purposes. This makes S-Benzyl-L-cysteine an essential tool in fine chemical manufacturing and custom synthesis projects.

Food Industry: In the food industry, S-Benzyl-L-cysteine is used as a flavoring agent due to its sulfur-containing side chain, which can contribute to savory and umami flavors. It is often added to enhance the taste of processed foods, soups, and seasoning blends. This application helps in improving the sensory qualities of food products while maintaining safety and regulatory standards.

Biochemical Research: S-Benzyl-L-cysteine is employed in biochemical studies to understand protein folding and stability. By incorporating this compound into protein structures, researchers can investigate the role of disulfide bonds in protein conformation and function. This knowledge is crucial for the development of protein-based therapeutics and understanding protein misfolding diseases such as Alzheimer’s and Parkinson’s.

1.Thermolysin as a catalyst in enzymatic synthesis of asparagine-containing peptides II.
Miranda MT1, Tominaga M. Int J Pept Protein Res. 1991 Feb;37(2):128-33.
Thermolysin was used as a catalyst to obtain the following protected di- and tripeptide esters: Z-Asn-Leu-OEt, Z-Asn-Phe-OEt, Moz-Asn-Leu-Gly-OEt, Boc-Asn-Leu-Gly-OEt, Z-Asn-Leu-Gly-OEt, Moz-Asn-Leu-Gly-OBzl, Moz-Asn-Leu-Gly-OtBu, Moz-Gln-Leu-Gly-OEt, Moz-Asn-Ile-Gly-OEt, and Moz-Asn-Leu-Ala-OEt. These compounds were obtained in pure form and the yields exceeded 50%, except for Moz-Asn-Leu-Gly-OtBu and Boc-Asn-Leu-Gly-OEt. H-Cys(Bzl)-OtBu and H-Cys(Bzl)-Pro-Leu-Gly-NH2 were both inadequate as amino components for obtaining Moz-Asn-Cys(Bzl)-OtBu, Z-Asn-Cys(Bzl)-OtBu and Moz-Asn-Cys(Bzl)-Pro-Leu-Gly-NH2 in the thermolysin-catalyzed reactions. In the attempted synthesis of the protected pentapeptide amide, this protease cleaved the Pro-Leu bond of the amino component H-Cys(Bzl)-Pro-Leu-Gly-NH2 and catalyzed the coupling between the resulting dipeptide amide and Moz-Asn-OH, thus yielding Moz-Asn-Leu-Gly-NH2 as the main product.
2.The effect of ε-aminocaproyl-S-benzyl-L-cysteine on the t-PA activity of human saliva.
Midura-Nowaczek K1, Kaczyńska J, Bruzgo I, Markowska A, Drozdowska D. Adv Med Sci. 2011;56(2):323-6. doi: 10.2478/v10039-011-0039-6.
PURPOSE: The aim of this work was to study the effect of the synthetic antifibrinolytics: ε-aminocaproic acid (EACA), tranexamic acid (AMCHA) and ε-aminocaproyl-S-benzyl-L-cysteine (H-EACA-S-Bzl-L-Cys-OH) on the fibrinolytic activity of saliva in order to obtain new data on the activity of saliva tissue plasminogen activator (t-PA).
Online Inquiry
Verification code
Inquiry Basket