Name: Boc-L-propraglycine dicyclohexylammonium salt
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

Boc-propargyl-L-Gly-OH DCHA; Boc-L-Pra-OH DCHA; (S)-2-(Boc-amino)-4-pentynoic acid dicyclohexylamine salt; Boc L Pra OH DCHA

IUPAC Name

N-cyclohexylcyclohexanamine;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-ynoic acid

Canonical SMILES

CC(C)(C)OC(=O)NC(CC#C)C(=O)O.C1CCC(CC1)NC2CCCCC2

InChI

InChI=1S/C12H23N.C10H15NO4/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;1-5-6-7(8(12)13)11-9(14)15-10(2,3)4/h11-13H,1-10H2;1,7H,6H2,2-4H3,(H,11,14)(H,12,13)/t;7-/m.0/s1

InChIKey

RUFMNUDFZKNXCE-ZLTKDMPESA-N

Melting Point

140-146 °C

Appearance

White powder

Storage

Store at 2-8 °C

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

Peptide Synthesis: Boc-L-proparglycine dicyclohexylammonium salt is commonly used as a building block in the synthesis of peptides. By protecting the amino group with the Boc (tert-butyloxycarbonyl) group, it allows for selective reactions at other sites. This compound is integral in creating complex peptide sequences for pharmaceutical and research purposes.

Drug Discovery: This compound is utilized in medicinal chemistry for the development of novel therapeutics. By incorporating Boc-L-proparglycine into peptide-based drug candidates, researchers can investigate the biological activity and therapeutic potential of these molecules. It provides a structural element that can influence the binding affinity and specificity of drug candidates.

Protein-Protein Interaction Studies: Boc-L-proparglycine is valuable in the study of protein-protein interactions, especially in designing probes and inhibitors. Researchers use it to synthesize modified peptides that can bind to target proteins, helping to elucidate interaction mechanisms. This information is pivotal for understanding complex biological processes and developing new therapeutic strategies.

Bioconjugation: The alkyne group of Boc-L-proparglycine allows for the introduction of additional chemical functionalities via click chemistry. This property is useful in the synthesis of bioconjugates, such as fluorescently labeled peptides or peptides conjugated to other biomolecules. Bioconjugates are instrumental in imaging, diagnostic applications, and targeted drug delivery systems.

1. 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.

2. Induction of apoptosis in K562 cells by dicyclohexylammonium salt of hyperforin through a mitochondrial-related pathway

Jin-Yun Liu, Zhong Liu, Dong-Mei Wang, Man-Mei Li, Shao-Xiang Wang, Rui Wang, Jian-Ping Chen, Yi-Fei Wang, De-Po Yang Chem Biol Interact. 2011 Apr 25;190(2-3):91-101. doi: 10.1016/j.cbi.2011.02.026. Epub 2011 Mar 3.

Hyperforin is an abundant phloroglucinol-type constituent isolated from the extract of the flowering upper portion of the plant Hypericum perforatum L. The dicyclohexylammonium salt of hyperforin (DCHA-HF) has exhibited antitumor and antiangiogenic activities in various cancer cells. Here, the antitumor effects of DCHA-HF on the chronic myeloid leukemia K562 cell line were investigated for the first time. DCHA-HF exhibited dose- and time-dependent inhibitory activities against K562 cells, with IC(50) values of 8.6 and 3.2 μM for 48 h and 72 h of treatment, respectively, which was more effective than that of the hyperforin. In contrast, little cytotoxic activity was observed with DCHA-HF on HUVECs. DCHA-HF treatment resulted in induction of apoptosis as evidenced from DNA fragmentation, nuclear condensation and increase of early apoptotic cells by DAPI staining analysis, TUNEL assay and Annexin V-FITC/PI double-labeled staining analysis, respectively. Moreover, DCHA-HF elicited dissipation of mitochondrial transmembrane potential that commenced with the release of cytochrome c through down-regulation of expression of anti-apoptotic proteins and up-regulation of expression of pro-apoptotic proteins. DCHA-HF treatment induced activation of the caspase 3, 8, and 9 cascade and subsequent PARP cleavage, and DCHA-HF-induced apoptosis was significantly inhibited by caspase inhibitors. Treated cells were arrested at the G1 phase of the cell cycle and the expression of p53 and p27(Kip1), two key regulators related to cell cycle and apoptosis, was up-regulated. These results suggest that DCHA-HF inhibits K562 cell growth by inducing caspase-dependent apoptosis mediated by a mitochondrial pathway and arresting the cell cycle at the G1 phase. Therefore, DCHA-HF is a potential chemotherapeutic antitumor drug for chronic myeloid leukemia therapy.

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.