S-Benzyl-L-cysteine methyl ester hydrochloride
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S-Benzyl-L-cysteine methyl ester hydrochloride

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Category
L-Amino Acids
Catalog number
BAT-004197
CAS number
16741-80-3
Molecular Formula
C11H15NO2S·HCl
Molecular Weight
261.80
S-Benzyl-L-cysteine methyl ester hydrochloride
IUPAC Name
methyl (2R)-2-amino-3-benzylsulfanylpropanoate;hydrochloride
Synonyms
L-Cys(Bzl)-OMe HCl; (R)-Methyl 2-Amino-3-(Benzylthio)Propanoate Hydrochloride
Appearance
White to off-white solid
Purity
≥ 99% (HPLC)
Melting Point
149-151 °C
Boiling Point
339.8°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H15NO2S.ClH/c1-14-11(13)10(12)8-15-7-9-5-3-2-4-6-9;/h2-6,10H,7-8,12H2,1H3;1H/t10-;/m0./s1
InChI Key
QVJDVOZRQMIIHP-PPHPATTJSA-N
Canonical SMILES
COC(=O)C(CSCC1=CC=CC=C1)N.Cl

S-Benzyl-L-cysteine methyl ester hydrochloride, a versatile biochemical compound, finds diverse applications in scientific research and industry. Here are four key applications:

Enzyme Inhibition Studies: Serving as an inhibitor in enzyme activity investigations, S-Benzyl-L-cysteine methyl ester hydrochloride plays a pivotal role in uncovering the inhibitory effects on specific enzymes. This deep dive into enzyme mechanisms and kinetics aids in the elucidation of crucial insights for the development of potential therapeutic enzyme inhibitors.

Drug Development: Positioned at the forefront of drug discovery, this compound is harnessed to unravel its pharmacological attributes and therapeutic potential. By exploring its interactions with biological targets, researchers can ascertain its efficacy and safety profiles, driving the exploration of novel drug candidates, particularly those targeting intricate biochemical pathways.

Peptide Synthesis: An essential player in peptide and protein synthesis, S-Benzyl-L-cysteine methyl ester hydrochloride acts as a protective shield for cysteine residues, safeguarding against undesirable reactions in the peptide assembly process. This meticulous approach ensures the production of top-tier, structurally precise peptides that are indispensable for both research endeavors and therapeutic interventions.

Biochemical Research: In the realm of general biochemical exploration, this compound serves as a key tool for delving into cysteine-related biochemical pathways. Researchers harness S-Benzyl-L-cysteine methyl ester hydrochloride to unravel the intricate roles of cysteine in protein functionality, redox biology, and cellular metabolism, paving the way for a deeper comprehension of the fundamental biological mechanisms that govern living organisms.

1. Rhodium(I) and rhodium(III) complexes formed by coordination and C-H activation of bulky functionalized phosphanes
Giuseppe Canepa, Carsten D Brandt, Kerstin Ilg, Justin Wolf, Helmut Werner Chemistry. 2003 Jun 6;9(11):2502-15. doi: 10.1002/chem.200204623.
The reaction of [[RhCl(C(8)H(14))(2)](2)] (2) with iPr(2)PCH(2)CH(2)C(6)H(5) (L(1)) led, via the isolated dimer [[RhCl(C(8)H(14))(L(1))](2)] (3), to a mixture of three products 4 a-c, of which the dinuclear complex [[RhCl(L(1))(2)](2)] (4 a) was characterized by Xray crystallography. The mixture of 4a-c reacts with CO, ethene, and phenylacetylene to give the square-planar compounds trans-[RhCl(L)(L(1))(2)] (L=CO (5), C(2)H(4) (6), C=CHPh (9)). The corresponding allenylidene(chloro) complex trans-[RhCl(=C=C=CPh(2))(L(1))(2)] (11), obtained from 4 a-c and HC triple bond CC(OH)Ph(2) via trans-[RhCl[=C=CHC(OH)Ph(2)](L(1))(2)] (10), could be converted stepwise to the related hydroxo, cationic aqua, and cationic acetone derivatives 12-14, respectively. Treatment of 2 and [[RhCl(C(2)H(4))(2)](2)] (7) with two equivalents of tBu(2)PCH(2)CH(2)C(6)H(5) (L(2)) gave the dimers [[RhCl(C(8)H(14))(L(2))](2)] (15) and [[RhCl(C(2)H(4))(L(2))](2)] (16), which both react with L(2) in the molar ratio of 1:2 to afford the five-coordinate aryl(hydrido)rhodium(III) complex [RhHCl(C(6)H(4)CH(2)CH(2)PtBu(2)-kappa(2)C,P)(L(2))] (17) by C-H activation. The course of the reactions of 17 with CO, H(2), PhC triple bond CH, HCl, and AgPF(6), leading to the compounds 19-21, 24, and 25 a, respectively, indicate that the coordinatively unsaturated isomer of 17 with the supposed composition [RhCl(L(2))(2)] is the reactive species. Labeling experiments using D(2), DCl, and PhC triple bond CD support this proposal. With either [Rh(C(8)H(14))(eta(6)-L(2)-kappaP]PF(6) or [Rh(C(2)H(4))(eta(6)-L(n)-kappaP]PF(6) (n=1 and 2) as the starting materials, the corresponding halfsandwich-type complexes 27, 28, and 32 were obtained. The nonchelating counterpart of the dihydrido compound 32 with the composition [RhH(2)(PiPr(3))(eta(6)-C(6)H(6))]PF(6) (35) was prepared stepwise from [Rh(C(2)H(4))(PiPr(3))(eta(6)-C(6)H(6))]PF(6) and H(2) in acetone via the tris(solvato) species [RhH(2)(PiPr(3))(acetone)(3)]PF(6) (34) as intermediate. The synthesis of the bis(chelate) complex [Rh(eta(4)-C(8)H(12))(C(6)H(5)OCH(2)CH(2)PtBu(2)-kappa(2)O,P)]BF(4) (39) is also described. Besides 4 a, the compounds 17, 25 a, and 39 have been characterized by Xray crystal structure analysis.
2. Hydroxymethylpyridine containing half-sandwich complexes of Rh(III), Ir(III) or Ru(II)
Daniel Carmona, Pilar Lamata, Antonio Sánchez, Pilar Pardo, Ricardo Rodríguez, Paola Ramírez, Fernando J Lahoz, Pilar García-Orduña, Luis A Oro Dalton Trans. 2014 Nov 7;43(41):15546-59. doi: 10.1039/c4dt02171a.
Complexes of the formula [(η(n)-ring)M(NOH){(R)-P1}][SbF6]2 ((η(n)-ring)M = (η(5)-C5Me5)Rh, (η(5)-C5Me5)Ir, (η(6)-p-MeC6H4iPr)Ru; NOH = hydroxymethylpyridine ligand; {(R)-P1} = (R)-monophos) have been prepared from the corresponding dimers [{(η(n)-ring)MCl}2(μ-Cl)2] through routes involving [(η(5)-C5Me5)RhCl2{(R)-P1}] or [(η(n)-ring)MCl(NOH)][SbF6] intermediates. The new complexes have been characterized by analytical and spectroscopic means, including the determination of the crystal structures of [(η(5)-C5Me5)IrCl2{(R)-P1}] (1b), [(η(6)-p-MeC6H4iPr)RuCl(NOH-1)][SbF6] (2c), [(η(5)-C5Me5)IrCl{(R)-NOH-2}][SbF6] ((R)-3b), [(η(5)-C5Me5)Rh(NOH-1){(R)-P1}][SbF6]2 (4a) and [(η(6)-p-MeC6H4iPr)Ru{(R)-NOH-2}{(S)-P1}][SbF6]2 ((R)-5c') by X-ray diffractometric methods. From NMR and X-ray data, the absolute configuration of the new chiral compounds was established.
3. Half-sandwich complexes of iridium and ruthenium containing cysteine-derived ligands
María Carmona, Ricardo Rodríguez, Fernando J Lahoz, Pilar García-Orduña, Carlos Cativiela, José A López, Daniel Carmona Dalton Trans. 2017 Jan 17;46(3):962-976. doi: 10.1039/c6dt04341k.
The dimers [{(ηn-ring)MCl}2(μ-Cl)2] ((ηn-ring)M = (η5-C5Me5)Ir, (η6-p-MeC6H4iPr)Ru) react with the modified cysteines S-benzyl-l-cysteine (HL1) or S-benzyl-α-methyl-l-cysteine (HL2) affording cationic complexes of the formula [(ηn-ring)MCl(κ2N,S-HL)]Cl (1, 2) in good yield. Addition of NaHCO3 to complexes 1 and 2 gave equilibrium mixtures of neutral [(ηn-ring)MCl(κ2N,O-L)] (3, 4) and cationic [(ηn-ring)M(κ3N,O,S-L)]Cl (6Cl, 7Cl) complexes. Similar mixtures were obtained in one-pot reaction by successive addition of the modified cysteine and NaHCO3 to the above formulated dimers. Addition of the N-Boc substituted cysteine derivative S-benzyl-N-Boc-l-cysteine (HL3) and NaHCO3 to the dimers [{(ηn-ring)MCl}2(μ-Cl)2] affords the neutral compounds [(ηn-ring)MCl(κ2O,S-L3)] ((ηn-ring)M = (η5-C5Me5)Ir (5a), (η6-p-MeC6H4iPr)Ru (5b)). Complexes of the formula [(ηn-ring)MCl(κ3N,O,S-L)][SbF6] (6Sb-8Sb), in which the cysteine derivative acts as a tridentate chelate ligand, can be prepared by adding one equivalent of AgSbF6 to the solutions of compounds 5 or to the mixtures of complexes 3/6Cl and 4/7Cl. The amide proton of compounds 8aSb and 8bSb can be removed by addition of NaHCO3 affording the neutral complexes [(ηn-ring)M(κ3N,O,S-L3-H)] ((ηn-ring)M = (η5-C5Me5)Ir (9a), (η6-p-MeC6H4iPr)Ru (9b)). Complexes 9a and 9b can also be prepared by reacting the dimers [{(ηn-ring)MCl}2(μ-Cl)2] with HL3 and two equivalents of NaHCO3. The absolute configuration of the complexes has been established by spectroscopic and diffractometric means including the crystal structure determination of (RIr,RC,RS)-[(η5-C5Me5)Ir(κ3N,O,S-L1)][SbF6] (6aSb). The thermodynamic parameters associated with the epimerization at sulphur that the iridium compound [(η5-C5Me5)Ir(κ3N,O,S-L3-H)] (9a) undergoes have been determined through variable temperature 1H NMR studies.
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