N-α-Allyloxycarbonyl-L-alanine dicyclohexylammonium salt
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N-α-Allyloxycarbonyl-L-alanine dicyclohexylammonium salt

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Category
L-Amino Acids
Catalog number
BAT-005948
CAS number
115491-98-0
Molecular Formula
C19H34N2O4
Molecular Weight
354.49
N-α-Allyloxycarbonyl-L-alanine dicyclohexylammonium salt
IUPAC Name
N-cyclohexylcyclohexanamine;(2S)-2-(prop-2-enoxycarbonylamino)propanoic acid
Synonyms
Aloc-Ala-OH DCHA; N-[(2-Propen-1-yloxy)carbonyl]-L-alanine dicyclohexylammonium salt; (2S)-2-[[(Prop-2-en-1-yloxy)carbonyl]amino]propanoic Acid dicyclohexylammonium salt; Alloc-Ala-OH DCHA; N-(Allyloxycarbonyl)alanine dicyclohexylammonium salt; N-Alloc-L-alanine DCHA; N-Allyloxycarbonyl-L-alanine DCHA; (S)-2-(((Allyloxy)carbonyl)amino)propanoic acid dicyclohexylammonium salt
Related CAS
90508-28-4 (free base)
Appearance
White Powder
Purity
≥95%
Melting Point
139-142 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C12H23N.C7H11NO4/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;1-3-4-12-7(11)8-5(2)6(9)10/h11-13H,1-10H2;3,5H,1,4H2,2H3,(H,8,11)(H,9,10)/t;5-/m.0/s1
InChI Key
WMDONTOVXUGLIK-ZSCHJXSPSA-N
Canonical SMILES
CC(C(=O)O)NC(=O)OCC=C.C1CCC(CC1)NC2CCCCC2

N-α-Allyloxycarbonyl-L-alanine dicyclohexylammonium salt, a specialized reagent for chemical synthesis and biochemistry, boasts diverse applications. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: Widely utilized in peptide synthesis, this compound serves as a safeguarding agent to shield the amino group during chain elongation, ensuring selective reactions of other functional groups for efficient peptide assembly. After synthesis completion, the dicyclohexylammonium salt facilitates easy removal of the protective group, streamlining the synthesis process.

Drug Development: Eminent in pharmaceutical research, N-α-Allyloxycarbonyl-L-alanine dicyclohexylammonium salt plays a crucial role in synthesizing complex molecule intermediates essential for designing novel drugs with enhanced efficacy and minimized side effects. By guaranteeing meticulous modifications of molecular structures, this compound is indispensable for optimizing drug activity and specificity.

Bioconjugation: Delving into bioconjugation techniques, researchers employ this compound to attach diverse biochemical moieties to peptides or proteins, a pivotal step in crafting biolabels, fluorescent markers, and therapeutic conjugates. Leveraging this salt enables stable and specific conjugation, augmenting the functional attributes of biomolecules with precision.

Protein Engineering: At the forefront of protein engineering, N-α-Allyloxycarbonyl-L-alanine dicyclohexylammonium salt facilitates site-specific mutations, enabling precise alterations of protein structures to explore their functions and interactions. This cutting-edge technology is instrumental in generating proteins with tailored properties for industrial or therapeutic purposes, pushing the boundaries of protein design and application.

1. 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.
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. 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].
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