N-Benzoyl-D-cysteine
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| Category | Others |
| Catalog number | BBF-05198 |
| CAS | 294856-85-2 |
| Molecular Weight | 225.26 |
| Molecular Formula | C10H11NO3S |
| Purity | >95% by HPLC |
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Specification
| Related CAS | 7217-84-7 (L-configuration) |
| Synonyms | D-Cysteine, N-benzoyl-; benzoyl-D-cysteine |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-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-/m1/s1 |
| InChI Key | LJWSDBHOEIBWJY-MRVPVSSYSA-N |
Properties
| Boiling Point | 486.7±40.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. 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.
2. Design, Synthesis, and Safener Activity of Novel Methyl (R)-N-Benzoyl/Dichloroacetyl-Thiazolidine-4-Carboxylates
Li-Xia Zhao, Hao Wu, Yue-Li Zou, Qing-Rui Wang, Ying Fu, Chun-Yan Li, Fei Ye Molecules. 2018 Jan 12;23(1):155. doi: 10.3390/molecules23010155.
A series of novel methyl (R)-N-benzoyl/dichloroacetyl-thiazolidine-4-carboxylates were designed by active substructure combination. The title compounds were synthesized using a one-pot route from l-cysteine methyl ester hydrochloride, acyl chloride, and ketones. All compounds were characterized by IR, ¹H NMR, 13C NMR, and HRMS. The structure of 4q was determined by X-ray crystallography. The biological tests showed that the title compounds protected maize from chlorimuron-ethyl injury to some extent. The ALS activity assay showed that the title compounds increased the ALS activity of maize inhibited by chlorimuron-ethyl. Molecular docking modeling demonstrated that Compound 4e competed against chlorimuron-ethyl to combine with the herbicide target enzyme active site, causing the herbicide to be ineffective.
3. Thioester deprotection using a biomimetic NCL approach
Valentina Villamil, Cecilia Saiz, Graciela Mahler Front Chem. 2022 Aug 22;10:934376. doi: 10.3389/fchem.2022.934376. eCollection 2022.
The reversibility of the thiol-thioester linkage has been broadly employed in many fields of biochemistry (lipid synthesis) and chemistry (dynamic combinatorial chemistry and material science). When the transthioesterification is followed by a S-to-N acyl transfer to give an amide bond, it is called Native Chemical Ligation (NCL), a high-yield chemoselective process used for peptide synthesis. Recently, we described thioglycolic acid (TGA) as a useful reagent for thioester deprotection both in solution and anchored to a solid-support under mild conditions. Inspired by NCL, in this work, we extended this approach and explored the use of 2-aminothiols for the deprotection of thiols bearing an acyl group. The best results were obtained using cysteamine or L-cysteine in an aqueous buffer pH 8 at room temperature for 30 min. The described approach was useful for S-acetyl, S-butyryl, and S-benzoyl heterocycles deprotection with yields up to 84%. Employing this methodology, we prepared six new analogs 2 of mercaptomethyl bisthiazolidine 1, a useful inhibitor of a wide-range of Metallo-β-Lactamases (MBLs). Compared with the previous methodologies (TGA polymer supported and TGA in solution), the biomimetic deprotection herein described presents better performance with higher yields, shorter reaction times, less time-consuming operations, easier setup, and lower costs.
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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 ╳
