Boc-S-tert-butyl-L-cysteine dicyclohexylammonium salt
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Boc-S-tert-butyl-L-cysteine dicyclohexylammonium salt

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Category
BOC-Amino Acids
Catalog number
BAT-002898
CAS number
60143-30-8
Molecular Formula
C12H23NO4S·C12H23N
Molecular Weight
458.71
Boc-S-tert-butyl-L-cysteine dicyclohexylammonium salt
IUPAC Name
(2R)-3-tert-butylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;N-cyclohexylcyclohexanamine
Synonyms
Boc-S-tert-butyl-L-cysteine dicyclohexylammonium salt; Dicyclohexylamine (R)-2-((tert-butoxycarbonyl)amino)-3-(tert-butylthio)propanoate
Appearance
White powder
Purity
≥ 98% (HPLC)
Melting Point
181-187 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C12H23NO4S.C12H23N/c1-11(2,3)17-10(16)13-8(9(14)15)7-18-12(4,5)6;1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h8H,7H2,1-6H3,(H,13,16)(H,14,15);11-13H,1-10H2/t8-;/m0./s1
InChI Key
CHFNEXOXGYAUEY-QRPNPIFTSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CSC(C)(C)C)C(=O)O.C1CCC(CC1)NC2CCCCC2

Boc-S-tert-butyl-L-cysteine dicyclohexylammonium salt is a chemical compound primarily used in peptide synthesis and biochemical research. Here are some key applications of Boc-S-tert-butyl-L-cysteine dicyclohexylammonium salt:

Peptide Synthesis: Boc-S-tert-butyl-L-cysteine dicyclohexylammonium salt is commonly used in the solid-phase synthesis of peptides. It serves as a protected form of cysteine, preventing unwanted reactions during the assembly of peptide chains. This ensures the integrity of the cysteine residues until they are selectively deprotected in later stages of synthesis.

Protein Engineering: In protein engineering, Boc-S-tert-butyl-L-cysteine dicyclohexylammonium salt is employed to introduce cysteine residues at specific positions in proteins. By incorporating these residues, researchers can create functional sites for disulfide bonds, enhancing protein stability and activity. This is crucial for developing therapeutic proteins, enzymes, and other biologically active molecules.

Bioconjugate Chemistry: This compound is useful in bioconjugate chemistry, where it facilitates the attachment of various functional groups to biomolecules. It allows for the site-specific modification of proteins and peptides, enabling the creation of conjugates with desired properties. Such applications are important in the development of targeted drug delivery systems and diagnostic tools.

Chemical Biology: Boc-S-tert-butyl-L-cysteine dicyclohexylammonium salt is valuable in chemical biology for studying protein function and interactions. By integrating this compound into proteins, researchers can probe the roles of cysteine residues and their modifications. This helps in elucidating the mechanisms of redox regulation, enzyme catalysis, and protein-protein interactions.

1. Dicyclo-hexyl-ammonium 3,5-dinitro-benzoate
Sohail Saeed, Naghmana Rashid, Rizwan Hussain, Wing-Tak Wong Acta Crystallogr Sect E Struct Rep Online. 2012 Jul 1;68(Pt 7):o2168. doi: 10.1107/S1600536812027389. Epub 2012 Jun 23.
The asymmetric unit of the title salt, C(12)H(24)N(+)·C(7)H(3)N(2)O(6) (-), contains two cations and two anions. In the crystal, the cations and anions are connected by N-H⋯O hydrogen bonds, forming a 12-membered ring with an R(4) (4)(12) graph-set motif. The center of this 12-membered ring coincides with an inversion centre. π-π stacking is observed between parallel benzene rings [centroid-centriod distance = 3.771 (2) Å].
2. The formation of 2-hydroxypropylmercapturic acid from 1-halogenopropanes in the rat
E A Barnsley Biochem J. 1966 Aug;100(2):362-72. doi: 10.1042/bj1000362.
1. 2-Hydroxypropylmercapturic acid, i.e. N-acetyl-S-(2-hydroxypropyl)-l-cysteine, has been isolated, as the dicyclohexylammonium salt, from the urine of rats dosed with 1-bromopropane. 2. The formation of the same metabolite from 1-chloropropane, 1-iodopropane, 1,2-epoxypropane and 1-chloropropan-2-ol has been demonstrated by chromatographic examination of the urine excreted by rats after they had been dosed with these compounds. 3. (+)- and (-)-Dicyclohexylammonium 2-hydroxypropylmercapturate have been prepared by fractional crystallization of the mixture of isomers obtained by two methods: the reaction of 1,2-epoxypropane with l-cysteine followed by acetylation, and the reduction of 2-oxopropylmercapturic acid. 4. The following compounds have also been prepared: S-(3-hydroxypropyl)-l-cysteine, (+)- and (-)-S-(2-hydroxypropyl)-l-cysteine, dicyclohexylammonium 3-hydroxypropylmercapturate, (+)- and (-)-dicyclohexylammonium 2-hydroxy-1-methylethylmercapturate, and (+)- and (-)-dicyclohexylammonium 1-(ethoxycarbonyl)ethylmercapturate.
3. Some metabolites of 1-bromobutane in the rabbit and the rat
S P James, D A Jeffery, R H Waring, P B Wood Biochem J. 1968 Oct;109(5):727-36. doi: 10.1042/bj1090727.
1. Rabbits and rats dosed with 1-bromobutane excrete in urine, in addition to butylmercapturic acid, (2-hydroxybutyl)mercapturic acid, (3-hydroxybutyl)mercapturic acid and 3-(butylthio)lactic acid. 2. Although both species excrete both the hydroxybutylmercapturic acids, only traces of the 2-isomer are excreted by the rabbit. The 3-isomer has been isolated from rabbit urine as the dicyclohexylammonium salt. 3. 3-(Butylthio)lactic acid is formed more readily in the rabbit; only traces are excreted by the rat. 4. Traces of the sulphoxide of butylmercapturic acid have been found in rat urine but not in rabbit urine. 5. In the rabbit about 14% and in the rat about 22% of the dose of 1-bromobutane is excreted in the form of the hydroxymercapturic acids. 6. Slices of rat liver incubated with S-butylcysteine or butylmercapturic acid form both (2-hydroxybutyl)mercapturic acid and (3-hydroxybutyl)mercapturic acid, but only the 3-hydroxy acid is formed by slices of rabbit liver. 7. S-Butylglutathione, S-butylcysteinylglycine and S-butylcysteine are excreted in bile by rats dosed with 1-bromobutane. 8. Rabbits and rats dosed with 1,2-epoxybutane excrete (2-hydroxybutyl)mercapturic acid to the extent of about 4% and 11% of the dose respectively. 9. The following have been synthesized: N-acetyl-S-(2-hydroxybutyl)-l-cysteine [(2-hydroxybutyl)mercapturic acid] and N-acetyl-S-(3-hydroxybutyl)-l-cysteine [(3-hydroxybutyl)mercapturic acid] isolated as dicyclohexylammonium salts, N-toluene-p-sulphonyl-S-(2-hydroxybutyl)-l-cysteine, S-butylglutathione and N-acetyl-S-butylcysteinyl-glycine ethyl ester.
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