Lysine derivatives

Lysine-Derived Alkaloids. Just as putresciae (36) derived from ornithine (23) is coasidered the pregenitor of the aucleus fouad ia pyrrolidine-containing alkaloids, so cadavetiae [462-94-2] (44), C H 4N2, derived from lysiae (24) is the idealized pregenitor of the 1-dehydropiperidine [28299-36-7] nucleus (45), C H N, found in the pomegranate, Sedum Dobelia, Dupin, and Lycopodium alkaloids (39). 

After secretion from the cell, certain lysyl residues of tropoelastin are oxidatively deaminated to aldehydes by lysyl oxidase, the same enzyme involved in this process in collagen. However, the major cross-links formed in elastin are the desmosines, which result from the condensation of three of these lysine-derived aldehydes with an unmodified lysine to form a tetrafunctional cross-hnk unique to elastin. Once cross-linked in its mature, extracellular form, elastin is highly insoluble and extremely stable and has a very low turnover rate. Elastin exhibits a variety of random coil conformations that permit the protein to stretch and subsequently recoil during the performance of its physiologic functions. 

FIGURE 3.3 Surface tension y plotted against the concentration c of lysine derivative 3.20. Critical aggregate concentration (O) cM=2430mg/L=2.43mM, yc =58mN/m. (Reprinted from Nalum Naess, S. et al., Chem. Phys. Lipids, 148, 63, 2007. With permission.)M... 

FIGURE 3.6 TEM photo of lysine derivative 3.20 showing an aggregate of rH = 100nm. (From Nalum Naess, S. and Elgseter, A., Trondheim, unpublished.)... 

The solubility of lysine derivative, 3.20, was measured at slightly over 180mg/mL, and molecular modeling also demonstrated potentially favorable plasma protein binding (Zsila et al. 2004). 

Berthelot T, Lain G, Latxague L, Deleris G (2004) Synthesis of novel fluorogenic L-Fmoc lysine derivatives as potential tools for imaging cells. J Fluoresc 14 671-675... 

Hallinan, E. A., Tsymbalov, S., Finnegan, P. M., Moore, W. M., Jerome, G. M., Currie, M. G., Pitzele, B. S., Acetamidine lysine derivative, N-(5(S)-amino-6,7-dihydroxyheptyl)ethanimidamide dihydrochloride a highly selective inhibitor of human inducible nitric oxide synthase, /. Med. Chem. 41 (1998), p. 775-777... 

Alkalization, 19 761-762 Alkaloids, 2 71-113 in coffee, 7 253 economic aspects, 2 107-109 lysine-derived, 2 80-82 major orders bearing, 2 75 miscellaneous types, 2 106-107 nitrogen introduction into terpenoid skeleton, 2 100-105 occurrence, detection, and isolation, 2 75-77... 

The reaction of the p-nitrophenyl esters with the polymer (4) was studied in dimethyl sulfoxide ( DMSO ) solution in the presence of triethylamine at 25°C. The poly-L-lysine derivatives obtained have different IR absorption spectra from those of the starting compounds, and have absorptions assigned to the nucleic acid bases. Poly( e,N-Ade-L-lysine )(5) was soluble in DMSO and ethylene glycol, and also in water below pH 3, where it was present as a protonated form. In dimethylformamide (... 

The contents of the nucleic acid bases in the poly-L-lysine derivatives were determined by UV spectra of the polymers after hydrolysis The polymers were hydrolyzed in 6 N-hydrochloric acid at 105°C for 24 hr, into lysine dihydrochloride and the carboxyethyl derivatives of the nucleic acid bases. The quantitative calculation was made relative to the standard sample of the carboxyethyl derivative of the nucleic acid bases. The analytical data are listed in Table 1. It was found that the thymine and uracil derivatives was completely substituted to polylysine. Low value in case of adenine base in the polymer may be attributed to the unstability of the activated ester, Ade-PNP (2), and may also be explained in terms of the steric interaction among bulky pendant groups of the polymer. When the poly-L-lysine containing about 50 mol % adenine units was again treated with Ade-PNP, the adenine unit content in the polymer increased up to 74 mol %(,] ). 

In relation to these works, the reaction of p-nitrophenyl esters with optically active poly( propyleneimine )(8) was studied at 25°C in DMSO solution according to the same procedure described for the case of poly-L-lysine derivatives. The poly( propyleneimine ) derivatives thus obtained have different IR and UV absorption spectra from those of the starting compounds, and show absorptions assigned to the nucleic acid bases. However, their contents determined by UV spectroscopy were substantially low as compared with the case of poly-L-lysine derivatives for (9) and (20), the base contents were below 30 and 50 %, respectively. The result was explained by a steric hindrance caused by methyl groups on the main chain of poly( propyleneimine ) ... 

Davis NR (1973) A method for the determination of lysine-derived collagen crosslinks. Biochem Biophys Res Comm 52, 877-883. 

The relationship between anemone fish, Amphiprion sp., and their sea anemone partners are regulated by alkaloids from the sea anemone. Amphiprion perideraion is attracted to the sea anemone Radianthus kuekenthali by the simple lysine-derived alkaloid amphikuemin (Fig. 12.6 Murata etal, 1986). Other simple alkaloids, aplysinopsin and dihydroaplysinopsin, also attract A. perideraion, regulate its swimming rate and induce their species-specific partnership. A related anemone fish, Amphiprion ocellaris, is attracted to the sea anemone Stoichactis kenti by tyramine (Fig. 12.6) and tryptamine induces searching by the fish (Murata etal, 1986). 

In the search for nonisotopic HDAC substrates, different fluorescence-labeled substrates have been developed, allowing for a convenient nonradioactive assay. The first described fiuorescence-based HDAC activity assay [21] uses the lysine-derived deacetylase substrate Boc(Ac)Lys-AMC, also called MAL (Figure 5.1). The incubation with a histone deacetylase preparation shows time-dependent conversion into its metabolite ML. 

In a very interesting paper Hu and Miller have described the synthesis of a L-lysine-derived cyclic hydroxamic acid 174 starting by the oxidation of protected Z-L-lysine 171 (formed from 170) with dimethyldioxirane (DMD) in acetone, followed by nitrone... 

L-lysine derived alkaloids Punicaceae Punica granatum Pelletierine Pseudopelletierine Methylpelletierine Anaferine... 

L-isoleucine L-leucine L-lysine Lysine-derived alkaloids Imidazole alkaloids Manzamine alkaloids True alkaloids... 

L-lysine furnishes alkaloids with at least four different nuclei. It is a protein amino acid, one of the most important alkaloid precursors. L-lysine-derived... 

It is lysine derivative of enalaprilat. Mechanism of action is same as other ACE inhibitors. After oral administration it is absorbed incompletely and slowly. 

Enalapril is an oral prodrug that is converted by hydrolysis to a converting enzyme inhibitor, enalaprilat, with effects similar to those of captopril. Enalaprilat itself is available only for intravenous use, primarily for hypertensive emergencies. Lisinopril is a lysine derivative of enalaprilat. Benazepril, fosinopril, moexipril, perindopril, quinapril, ramipril, and trandolapril are other long-acting members of the class. All are prodrugs, like enalapril, and are converted to the active agents by hydrolysis, primarily in the liver. 

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