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N-α-Carbobenzoxy-β-cyclohexyl-L-alanine dicyclohexylammonium salt

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

Category

CBZ-Amino Acids

Catalog number

BAT-006937

CAS number

54594-40-0

Molecular Formula

C29H46N2O4

Molecular Weight

486.70

N-α-Carbobenzoxy-β-cyclohexyl-L-alanine dicyclohexylammonium salt

IUPAC Name

N-cyclohexylcyclohexanamine;(2S)-3-cyclohexyl-2-(phenylmethoxycarbonylamino)propanoic acid

Synonyms

Z-Cha-OH DCHA; Z-Phe(hexahydro)-OH DCHA; N-α-Carbobenzoxy-hexahydro-L-phenylalanine dicyclohexylammonium salt

Related CAS

25341-42-8 (free base)

Storage

Store at 2-8 °C

InChI

InChI=1S/C17H23NO4.C12H23N/c19-16(20)15(11-13-7-3-1-4-8-13)18-17(21)22-12-14-9-5-2-6-10-14;1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h2,5-6,9-10,13,15H,1,3-4,7-8,11-12H2,(H,18,21)(H,19,20);11-13H,1-10H2/t15-;/m0./s1

InChI Key

IDRYYPLNVRWFOR-RSAXXLAASA-N

Canonical SMILES

C1CCC(CC1)CC(C(=O)O)NC(=O)OCC2=CC=CC=C2.C1CCC(CC1)NC2CCCCC2

N-α-Carbobenzoxy-β-cyclohexyl-L-alanine dicyclohexylammonium salt is a specialized reagent utilized in a myriad of biochemical applications. Explore its diverse applications with a twist of high perplexity and burstiness:

Peptide Synthesis: Within the realm of solid-phase peptide synthesis, N-α-Carbobenzoxy-β-cyclohexyl-L-alanine dicyclohexylammonium salt emerges as a shielded amino acid essential for crafting intricate peptide sequences. Acting as a vigilant guardian of amino groups, this reagent meticulously blocks unwanted reactions during peptide construction enabling the precise assembly of complex peptide structures with finesse.

Protease Inhibition Studies: Engage in cutting-edge research on protease inhibitors where this compound serves as a versatile substrate for probing enzyme-substrate dynamics. By harnessing the power of this reagent, scientists delve deep into the realms of protease specificity and activity laying the foundation for innovative therapeutic inhibitors targeting diseases characterized by protease dysregulation including cancer and infectious ailments.

Pharmaceutical Development: Embark on a journey through pharmaceutical innovation as N-α-Carbobenzoxy-β-cyclohexyl-L-alanine dicyclohexylammonium salt emerges as a cornerstone for synthesizing groundbreaking drug candidates. With its unique structural properties, this compound unlocks the realm of peptidomimetics-compounds mirroring peptide functions but boasting superior stability and bioavailability. These peptidomimetics stand as pillars in drug development offering targeted solutions for a spectrum of medical conditions.

Structural Biology: Dive into the intricate world of structural biology where the incorporation of N-α-Carbobenzoxy-β-cyclohexyl-L-alanine derivatives elevates the crystallization of peptides and proteins to new heights. Through harnessing the power of this compound researchers enhance the crystalline structure and stability of proteins paving the way for unraveling molecular complexities via X-ray crystallography. Unveil the secrets of protein function driving advancements in drug design and therapeutic interventions.

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. 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.

3. 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.