Boc-3-styryl-L-alanine dicyclohexylamine salt
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Boc-3-styryl-L-alanine dicyclohexylamine salt

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Category
BOC-Amino Acids
Catalog number
BAT-007021
CAS number
261165-04-2
Molecular Formula
C16H21NO4·C12H23N
Molecular Weight
472.67
Boc-3-styryl-L-alanine dicyclohexylamine salt
Synonyms
Boc-L-Ala(styryl)-OH DCHA; (S)-3-(Boc-amino)-5-phenyl-4-pentenoic acid dicyclohexylamine salt
Appearance
White powder
Purity
≥ 99% (HPLC)
Melting Point
103-106 °C
Boiling Point
498.1°C at 760 mmHg
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/b10-7+;/t13-;/m0./s1
InChI Key
XFECITMZVLWAJB-LIGCKOFKSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC=CC1=CC=CC=C1)C(=O)O.C1CCC(CC1)NC2CCCCC2

Boc-3-styryl-L-alanine dicyclohexylamine salt. a highly specialized chemical compound utilized in a myriad of research and industrial settings, exhibits remarkable versatility and importance. Here are the key applications intricately detailed with high perplexity and burstiness:

Peptide Synthesis: A staple in peptide synthesis, this compound functions as a protected amino acid derivative with the Boc (tert-butoxycarbonyl) group acting as a pivotal shield for the amino group, This protective role facilitates the seamless assembly of peptides in solid-phase peptide synthesis (SPPS) culminating in the creation of intricate peptide structures. Subsequent removal of the Boc group unveils the meticulously crafted peptide ready for further exploration and application.

Drug Discovery: Positioned at the forefront of drug innovation, Boc-3-styryl-L-alanine dicyclohexylamine salt plays a vital role in the design and synthesis of novel pharmaceutical compounds. Its intricately designed molecular structure serves as a playground for researchers delving into the complex realm of structure-activity relationships (SAR) in medicinal chemistry. By harnessing the unique properties of this compound scientists craft cutting-edge drug candidates poised to deliver therapeutic breakthroughs.

Enzyme Inhibition Studies: Delving deep into the intricacies of enzyme-substrate interactions and inhibition mechanisms, researchers turn to Boc-3-styryl-L-alanine dicyclohexylamine salt as a versatile tool. Whether as a substrate analog or a potent inhibitor in enzyme assays, this compound unveils valuable insights into enzyme kinetics and function unraveling the intricate dance of biochemical reactions. Such studies lay the foundation for crafting potent enzyme inhibitors with profound implications for pharmaceutical interventions.

Chemical Biology: At the crossroads of chemistry and biology, this compound emerges as a pivotal player in unraveling protein interactions and biological pathways. By integrating Boc-3-styryl-L-alanine into peptide-based probes, scientists embark on a journey to decode the complexities of protein functions and interactions within cellular contexts. This approach not only sheds light on the convoluted processes underlying life but also pinpoints potential targets for therapeutic interventions paving the way for transformative biomedical discoveries.

1.Spectrophotometric and chromatographic determination of insensitive energetic materials: HNS and NTO, in the presence of sensitive nitro-explosives.
Can Z1, Uzer A, Tekdemir Y, Erçağ E, Türker L, Apak R. Talanta. 2012 Feb 15;90:69-76. doi: 10.1016/j.talanta.2011.12.077. Epub 2012 Jan 4.
As there are no molecular spectroscopic determination methods for the most widely used insensitive energetic materials, 2,2',4,4',6,6'-hexanitrostilbene (HNS) and 3-nitro-1,2,4-triazole-5-one (NTO), in the presence of sensitive nitro-explosives, two novel spectrophotometric methods were developed. For HNS and TNT mixtures, both analytes react with dicyclohexylamine (DCHA) forming different colored charge-transfer complexes, which can be resolved by derivative spectroscopy. The spectrophotometric method for NTO measures the 416-nm absorbance of its yellow-colored Na(+)NTO(-) salt formed with NaOH. TNT, if present, is pre-extracted into IBMK as its Meisenheimer anion forming an ion-pair with the cationic surfactant cetyl pyridinium (CP(+)) in alkaline medium, whereas the unextracted NTO is determined in the aqueous phase. The molar absorptivity (ε, L mol(-1)cm(-1)) and limit of quantification (LOQ, mg L(-1)) are as follows: for HNS, ε=2.75 × 10(4) and LOQ=0.
2.Topical anti-inflammatory activity of extracts and compounds from Hypericum perforatum L.
Sosa S1, Pace R, Bornancin A, Morazzoni P, Riva A, Tubaro A, Della Loggia R. J Pharm Pharmacol. 2007 May;59(5):703-9.
Three preparations of Hypericum perforatum L. (a hydroalcoholic extract, a lipophilic extract and an ethylacetic fraction) and the pure compounds hypericin, adhyperforin, amentoflavone, hyperoside, isoquercitrin, hyperforin dicyclohexylammonium (DHCA) salt and dicyclohexylamine were evaluated for their topical anti-inflammatory activity. H. perforatum preparations provoked a dose-dependent reduction of Croton-oil-induced ear oedema in mice, showing the following rank order of activity: lipophilic extract > ethylacetic fraction > hydroalcoholic extract (ID50 (dose that inhibited oedema by 50%) 220, 267 and >1000 microg cm(-2), respectively). Amentoflavone (ID50 0.16 micromol cm(-2)), hypericin (ID50 0.25 micromol cm(-2)), hyperforin DHCA salt (ID50 0.25 micromol cm(-2)) and adhyperofrin (ID50 0.30 micromol cm(-2)) had anti-inflammatory activity that was more potent or comparable to that of indometacin (ID50 0.26 micromol cm(-2)), whereas isoquercitrin and hyperoside were less active (ID50 about 1 micromol cm(-2)).
3.In-vitro antitumor activity evaluation of hyperforin derivatives.
Sun F1, Liu JY, He F, Liu Z, Wang R, Wang DM, Wang YF, Yang DP. J Asian Nat Prod Res. 2011 Aug;13(8):688-99. doi: 10.1080/10286020.2011.584532.
The derivatives of hyperforin, namely hyperforin acetate (2), 17,18,22,23,27,28,32,33-octahydrohyperforin acetate (3), and N,N-dicyclohexylamine salt of hyperforin (4), have been investigated for their antitumor properties. In-vitro studies demonstrated that 2 and 4 were active against HeLa (human cervical cancer), A375 (human malignant melanoma), HepG2 (human hepatocellular carcinoma), MCF-7 (human breast cancer), A549 (human nonsmall cell lung cancer), K562 (human chronic myeloid leukemia), and K562/ADR (human adriamycin-resistant K562) cell lines with IC(50) values in the range of 3.2-64.1 μM. The energy differences between highest occupied molecular orbital and lowest unoccupied molecular orbital of 2-4 were calculated to be 0.39778, 0.43106, and 0.30900 a.u., respectively, using the Gaussian 03 software package and ab initio method with the HF/6-311 G* basis set. The result indicated that the biological activity of 4 might be the strongest and that of 3 might be the weakest, which was in accordance with their corresponding antiproliferative effects against the tested tumor cell lines.
4.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.
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