L-Lysine Synthesis

A similar reaction is catalyzed by homoaconitate hydratase (E.C. 4.2.1.36), which is an enzyme from the L-lysine synthesis that forms homocitric acid (2-hydrox-ybutane-l,2,4-tricarboxylic acid, 17) from homo-ris-aconitate (16)The enzyme 2-methylcitrate dehydratase (E. C. 4.2.1.79) catalyzes the addition of water to (Z)-but-2-ene-l,2,3-tricarboxylic acid (18) to yield 2-methylcitric acid (2-hydroxybutane-... 

A further flux control step within L-lysine synthesis is the aspartate semialdehyde branch point. The aldehyde is either used as a substrate for the homoserine dehydrogenase, or together with pyruvate as a substrate for the dihydrodipicolinate synthase (Fig. 10). Whereas the homoserine dehydrogenase is allosterically controlled in its catalytic activity by the L-threonine concentration... 

Boustta, M., Huguet, J., and Vert, M., 1991, New functional polyamides derived from citric acid and L-lysine Synthesis and characterization, Makromol. Chem., Macromol. Symp., 47 345-355... 

Dinitrophenyl-i.-diaminobutyric acid hydrazide dihydrobromide, 503 7-Dinitrophenyl-L-diaminobutyric acid hydrochloride, synthesis of, 502 7-Dinitrophenyl-L-diaminobutyric acid methyl ester hydrochloride, 502, 503 Af -Dinitrophenyl-AT -bromoacetyl-D-lysine, synthesis of, 490 iV -Dinitrophenyl-iV -bromoacetyl-L-lysine, synthesis of, 490 Ar -Dinitrophenyl-JV -bromoacetyl-L-omithine, synthesis of, 490 iV-Dinitrophenyl-iV -Z-ethylenediamine, nthesis of, 489... 

Zhou, L.B. and Zeng, A.P. (2015) Exploring lysine riboswiteh for metabolic flux control and improvement of L-lysine synthesis in Corynehacterium glutamicum. ACS Synth. Biol, 4 (6), 729-734. 

Scheme 17 Synthesis of water-soluble EG-grafted poly(L-lysine)s...

Cardinaux F, Howard JC, Taylor GT, Scheraga HA (1977) Block copolymers of amino-acids. 1. Synthesis and stmcture of copolymers of L-alanine or L-phenylalanine with D, L-lysine-D7 or D, L-lysine. Biopolymers 16 2005-2028... 

Chapman et al. [131] reported the synthesis of poly(ethylene oxide) (PEO) supported dendritic f-BOC-poly(a, c-L-lysines). These dendritic polymers termed as hydramphiphiles formed foams possessing good temporal stability in aqueous solution. Scrimin et al. [132] synthesized a three-directional polypeptide having uses in membrane permeability modulation. Decapeptide fragments were linked to TREN [tris(2-aminoethyl)amine] core. 

Berthelot, T, Talbot, J. C, Lain, G, Deleris, G. and Latxague, L. (2005). Synthesis of N epsilon-(7-diethylaminocoumarin-3-carboxyl)-and N epsilon-(7-methoxycoumarin-3-carboxyl)-L-Fmoc lysine as tools for protease cleavage detection by fluorescence. J. Pept. Sci. 11,153-160. 

S. Gac, J. Coudane, M. Boustta, M. Domurado, and M. Vert, Synthesis, characterization and in vivo behavior of a norfloxacin-poly(L-lysine citramide imide) conjugate bearing mannosyl residues, J. Drug Targeting, 1 (2000) 393 -06. 

Qualmann, B., Kessels, M.M., Musiol, H.J., Sierralta, W.D., Jungblut, P.W., and Morodeg L. (1996) Synthesis of boron-rich lysine dendrimers as protein labels in electron microscopy. Angew. Chem. Int. 

R Schwyzer, B Rittel. Synthesis of intermediates for a corticotropic nonadecapeptide. I. A, -ferf-Butoxycarbonyl-L-lysine, A a(M-/c rt-biitoxycarbonyl-i,-lysyl)-/Vr-/< rt-butoxycarbonyl-L-lysine, M-tert-butoxycarbonyl-L-lysyl-i.-prolyl-i.-valylglycine and derivatives. Helv Chim Acta 44, 159, 1961. 

NL Benoiton, RE Demayo, GJ Moore, JR Coggins. A modified synthesis of tx-V-car-bobenzoxy-L-lysine and the preparation and analysis of mixtures of ( -V-methyl-lysines). (diazomethane) Can J Biochem 49, 1292, 1971. 

Synthesis of Poly-L-Lysine Containing Nucleic Acid Bases... 

Table 3. Synthesis and properties of nucleic acid base substituted L-lysines...

Figure 10.2 Enzyme-coupled system for synthesis of r-pipecoUc acid from L-lysine...

A Streptomyces enzyme that catalyzes hydrolysis of capsaicin is described by Koreishi et The substrate is an A -vanillyl aliphatic amide, and the authors found that their enzyme also accepted A lauroyl amino acids as substrates. The enzyme was used successfully to catalyze the reaction in the opposite direction, driving the equilibrium toward synthesis by running it in buffer containing 78% glycerol. Yields of 5-40% were obtained for a wide range of natural L-amino acids. In the case of L-lysine the enzyme catalyzed acylation at both amino groups, with a clear preference for the e-NH2. 

Naimochelin C (Fig. 15, 54) from the myxobacterium Nannocystis exedens contains two L-Lys and two ( )-cinnamic acid units. The reported mono- and di-methyl esters (nannochelin B and A) may be artifacts from the work-up (198). A synthesis is described (29) (see Sect. 8.4). The ochrobactins (Fig. 15,55) isolated from the sea-shore bacterium Ochrobactrum sp. (214) with the spacer L-lysine are membrane active due to the fatty acid residues (saturated Cg and (2 )-unsaturated Cg and Cio) cf. lipopeptidic siderophores in Sect. 2.8. 

Scheme 2.16 Synthesis of cyclic amino acid (R)-40 by combined use of L-lysine oxidase and NMAADH.

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