BoC-D-Styrylalanine dicyclohexylamine salt
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BoC-D-Styrylalanine dicyclohexylamine salt

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Category
BOC-Amino Acids
Catalog number
BAT-014110
CAS number
261380-19-2
Molecular Formula
C28H44N2O4
Molecular Weight
472.66
BoC-D-Styrylalanine dicyclohexylamine salt
IUPAC Name
N-cyclohexylcyclohexanamine;2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpent-4-enoic acid
Synonyms
Boc-D-Ala(styryl)-OH DCHA; (R)-2-(Boc-amino)phenyl-4-pentenoic acid dicyclohexylamine salt; Boc-3-styryl-D-alanine dicyclohexylamine salt
Appearance
white powder
Purity
95%
Density
1.1049 (rough estimate)
Boiling Point
433.35°C (rough estimate)
Storage
Store at 2-8 °C
InChI
InChI=1S/C16H21NO4.C12H23N/c1-16(2,3)21-15(20)17-13(14(18)19)11-7-10-12-8-5-4-6-9-12;1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h4-10,13H,11H2,1-3H3,(H,17,20)(H,18,19);11-13H,1-10H2
InChI Key
XFECITMZVLWAJB-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC=CC1=CC=CC=C1)C(=O)O.C1CCC(CC1)NC2CCCCC2

BoC-D-Styrylalanine dicyclohexylamine salt, a versatile chemical compound, finds wide applications in peptide synthesis and diverse biochemical uses. Here are the key applications of this compound elucidated with a high degree of perplexity and burstiness:

Peptide Synthesis: An indispensable component in peptide chain assembly, Boc-D-Styrylalanine dicyclohexylamine salt serves as an essential amino acid derivative. Scientists leverage this compound in solid-phase peptide synthesis crafting specific sequences that offer insights into protein functionalities and interplay. Its exceptional stability and reactivity make it a preferred choice for generating exceptionally pure peptides in controlled laboratory environments.

Drug Development: Unleashing a wave of innovation in pharmaceutical exploration, Boc-D-Styrylalanine dicyclohexylamine salt plays a pivotal role in designing and synthesizing novel drugs. By integrating this compound into peptide configurations, researchers can forge promising drug candidates with enhanced efficacy and bioavailability. This process not only aids in pinpointing new drug targets but also streamlines the optimization of crucial drug attributes setting the stage for groundbreaking therapeutic solutions.

Proteomics Studies: In the realm of proteomics, Boc-D-Styrylalanine dicyclohexylamine salt emerges as a prized asset for labeling peptides during mass spectrometry investigations. This practice streamlines the detection and quantification of proteins and their post-translational modifications enhancing overall analysis sensitivity and resolution. By leveraging this compound researchers gain deeper insights into the intricate structures and functions of proteins paving the way for cutting-edge advancements in the field.

Bioconjugation: At the forefront of bioconjugation techniques, Boc-D-Styrylalanine dicyclohexylamine salt acts as a critical linchpin in linking peptides to diverse biomolecules like antibodies or fluorescent dyes. This strategic coupling enables the development of sophisticated diagnostic instruments and biosensors propelling the elucidation of molecular interactions and cellular processes with unparalleled precision and accuracy. By harnessing this compound researchers unlock a realm of possibilities for tracking and deciphering intricate biological pathways.

1.In vitro evaluation of the clastogenicity of fumagillin.
Stevanovic J1, Stanimirovic Z, Radakovic M, Stojic V. Environ Mol Mutagen. 2008 Oct;49(8):594-601. doi: 10.1002/em.20409.
Fumagillin, an antibiotic compound produced by Aspergillus fumigatus, is effective against microsporidia and various Amoeba species, but is also toxic when administered systemically to mammals. Furthermore, a recent in vivo study by Stanimirovic Z et al. 2007: (Mutat Res 628:1-10) indicated genotoxic effects of fumagillin. The aim of the present study was to investigate and explain the clastogenic effects of fumagillin (in the form of fumagillin dicyclohexylamine salt) on human peripheral blood lymphocytes in vitro by sister-chromatid exchanges (SCE), chromosome aberrations (CA), and micronucleus (MN) tests. The mitotic index (MI), proliferation index (PI), and nuclear division index (NDI) were calculated to evaluate the cytotoxic potential of fumagillin. Five concentrations of fumagillin (0.34, 0.68, 1.02, 3.07, and 9.20 microg/ml) were applied to lymphocyte cultures. All the tested concentrations of fumagillin increased the frequency of SCE per cell significantly (P < 0.
2.Stability of dicyclohexylamine and fumagillin in honey.
van den Heever JP1, Thompson TS2, Curtis JM3, Pernal SF4. Food Chem. 2015 Jul 15;179:152-8. doi: 10.1016/j.foodchem.2015.01.111. Epub 2015 Jan 31.
Fumagillin is extensively used to control nosema disease in apiculture. In the commercial formulation, fumagillin is present as a salt in an equimolar quantity with dicyclohexylamine (DCH). In this study DCH was observed to be significantly more resistant to degradation in honey than fumagillin using LC-MS/MS analysis. Observed half-lives for DCH ranged from a minimum of 368 days when kept at 34 °C in darkness, to a maximum of 852 days when stored at 21 °C in darkness. A maximum half-life of 246 days was observed for fumagillin in samples kept in darkness at a temperature of 21 °C. The observed half-life of fumagillin was estimated to be 3 days when exposed to light at 21 °C, and complete decomposition was observed after 30 days under the same conditions. The stability of DCH, combined with its genotoxicity and tumorigenic properties make it an important potential contaminant in honey destined for human consumption.
3.Structure-property correlation of a new family of organogelators based on organic salts and their selective gelation of oil from oil/water mixtures.
Trivedi DR1, Ballabh A, Dastidar P, Ganguly B. Chemistry. 2004 Oct 25;10(21):5311-22.
Organic salts based on dicyclohexylamine and substituted/unsubstituted cinnamic acid exhibit efficient gelation of organic fluids, including selective gelation of oil from an oil/water mixture. Among the cinnamate salts, dicyclohexylammonium 4-chlorocinnamate (1), 3-chlorocinnamate (2), 4-bromocinnamate (3), 3-bromocinnamate (4), 4-methylcinnamate (5) and the parent cinnamate (6) are gelators, whereas 2-chlorocinnamate (7), 2-bromocinnamate (8), 3-methylcinnamate (9), 2-methylcinnamate (10) and hydrocinnamate (11) are non-gelators. Non-gelation behaviour of 11 and various benzoate derivatives 12-18 indicate the significance of an unsaturated backbone in the gelation behaviour of the cinnamate salts. A structure-property correlation based on the single-crystal structures of most of the gelators (1, 3, 5 and 6) and non-gelators, such as 7, 8, 10-18, indicates that the prerequisite for the one-dimensional (1D) growth of the gel fibrils is mainly governed by the 1D hydrogen-bonded network involving the ion pair.
4.Diastereoselective arylithium addition to an alpha-trifluoromethyl imine. Practical synthesis of a potent cathepsin K inhibitor.
Roy A1, Gosselin F, O'Shea PD, Chen CY. J Org Chem. 2006 May 26;71(11):4320-3.
A practical, chromatography-free synthesis of potent cathepsin K inhibitor 1 is described. The addition of 4-bromophenyllithium to an alpha-trifluoromethylimine derived from commercially available (S)-leucinol was accomplished in a highly diastereoselective manner (97.6% de, 91% yield). Subsequent Suzuki cross-coupling afforded biaryl 7. Oxidation of the alcohol and sulfide functionalities led to the formation of carboxylic acid 8. Crystallization of 7 and acid 8 as its dicyclohexylamine salt gave excellent impurity rejection. The final amide coupling with commercially available aminoacetonitrile hydrochloride afforded 1 in excellent purity (99.6A% by HPLC, 100% de, <3 ppm Pd, W, Cr).
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