N-Benzoyl-L-cysteine
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| Category | Others |
| Catalog number | BBF-05218 |
| CAS | 7217-84-7 |
| Molecular Weight | 225.26 |
| Molecular Formula | C10H11NO3S |
| Purity | >95% by HPLC |
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Specification
| Related CAS | 294856-85-2 (D-configuration) |
| Synonyms | L-Cysteine, N-benzoyl-; Bz-L-Cys-OH; benzoyl-L-cysteine |
| Storage | Store at -20°C |
| IUPAC Name | (2R)-2-benzamido-3-sulfanylpropanoic acid |
| Canonical SMILES | C1=CC=C(C=C1)C(=O)NC(CS)C(=O)O |
| InChI | InChI=1S/C10H11NO3S/c12-9(7-4-2-1-3-5-7)11-8(6-15)10(13)14/h1-5,8,15H,6H2,(H,11,12)(H,13,14)/t8-/m0/s1 |
| InChI Key | LJWSDBHOEIBWJY-QMMMGPOBSA-N |
Properties
| Boiling Point | 486.7±40.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. The synthesis and structure of the derivatives of 2-deoxy-2-hydroxyimino-D-lyxo-hexopyranosyl-L-cysteine and -thiophenol
B Liberek, A Konitz, R Frankowski, Z Smiatacz Carbohydr Res. 2000 Jun 2;326(2):151-8. doi: 10.1016/s0008-6215(00)00035-5.
3,4,6-Tri-O-acetyl-2-deoxy-2-hydroxyimino-beta and -alpha-D-lyxo-hexopyranosides of thiophenol (3, 4) and the methyl ester of N-benzoyl-L-cysteine have been synthesised by condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-alpha-D-galactopyranosyl chloride with thiophenol and the L-cysteine derivative, respectively. The conformation of the sugar residue and configuration of the anomeric centre as well as of the hydroxyimino group were established on the basis of the 1H NMR (DQF-COSY, ROESY, TOCSY) spectrometric techniques and polarimetric data. Additionally, the structure of S-[3,4,6-tri-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-beta-D-lyxo -hexopyranosyl]-thiophenol (3) was supported by X-ray diffraction data.
2. Amide compound synthesis by adenylation domain of bacillibactin synthetase
Tomoko Abe, Yoshiteru Hashimoto, Sayaka Sugimoto, Kenta Kobayashi, Takuto Kumano, Michihiko Kobayashi J Antibiot (Tokyo). 2017 Apr;70(4):435-442. doi: 10.1038/ja.2016.117. Epub 2016 Oct 12.
The adenylation domain of nonribosomal peptide synthetase (NRPS) is responsible for the selective substrate recognition and its activation (as an acyl-O-AMP intermediate) during ATP consumption. DhbE, a stand-alone adenylation domain, acts on an aromatic acid, 2,3-dihydroxybenzoic acid (DHB). This activation is the initial step of the synthesis of bacillibactin that is a high-affinity small-molecule iron chelator also termed siderophore. Subsequently, the activated DHB is transferred and attached covalently to a peptidyl carrier protein domain via a thioester bond. Adenylation domains belong to the superfamily of adenylate-forming enzymes including acetyl-CoA synthetase, acyl-CoA synthetase and firefly luciferase. We previously reported a novel N-acylation reaction for an acyl-CoA synthetase (AcsA) that originally catalyzes the formation of a thioester bond between an acid and CoA, yielding acyl-CoA. This novel reaction was also confirmed for acetyl-CoA synthetase and firefly luciferase, but not yet for an adenylation domain. Here, we for the first time demonstrated the synthesis of N-acyl-L-cysteine by a stand-alone adenylation domain, DhbE. When DHB and L-cysteine were used as substrates of DhbE, N-DHB-L-cysteine was formed. A Vmax value of 0.0156±0.0008 units mg-1 and Km values of 150±18.3 mM for L-cysteine and 0.0579±0.0260 mM for DHB were obtained in this novel reaction. Furthermore, DhbE synthesized N-benzoyl-L-cysteine when benzoic acid and L-cysteine were used as substrates. Through the N-acylation reaction of DhbE, we also succeeded in the synthesis of N-aromatic acyl compounds that have never previously been reported to be produced by this enzymatic method.
3. Chiral Recognition by Flexible Coordination Polymers of Ag+ with a Cysteine-Based Chiral Thiol Ligand That Bears a Binding Site
Su-Li Dong, Yan Xu, Yin-Zhu Chen, Xiao-Sheng Yan, Zhao Li, Jian-Wei Xie, Yun-Bao Jiang Inorg Chem. 2021 Apr 19;60(8):5413-5418. doi: 10.1021/acs.inorgchem.1c00104. Epub 2021 Mar 31.
We report a new scheme for chiral recognition using coordination polymers of Ag+ with a chiral thiol ligand that contains a binding group. N-Benzoyl-l-cysteine ethyl ester equipped with a boronic acid group at the para position of the phenyl ring forms coordination polymers with Ag+ in alkaline aqueous solutions that exhibit excellent selectivity toward a d-glucose enantiomer over l-glucose, while the coordination polymers from the d-cysteine-based thiol ligand are specific for l-glucose. It is assumed that a conformation change occurs upon interaction of a saccharide molecule with the polymeric chain receptor, for which the next binding is promoted, leading to the highly effective chiral recognition, despite the flexible nature of the polymeric receptor.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
