A amino adipate

Bailey AJ, Ranta MH, Nicholls AC, Partridge SM and Elsden DP (1977) Isolation of a -amino adipic acid from mature dermal collagen and elastin. Evidence for an oxidative pathway in the maturation of collagen and elastin. Biochem Biophys Res Comm 78, 1403-1410. 

The next member of this homologous series, a-amino-adipic acid, has been prepared by Sorensen from phthalimidosodium malonic ester and chlorobutyronitrile in the following way —... 

Table 2.1.8 The primary defects of amino acid metabolism and the corresponding changes of plasma or urine amino acid levels. AA amino acid, AAA a-amino-adipic acid,...

P-Lactam Antibiotics.—The tripeptide [as (159)] isolated from Penicillium chry-sogenum151 has been accepted as a likely key intermediate in the biosynthesis of penicillins with penicillin N (158), the first of the fi -lactams to be formed.152 It has been shown recently that this tripeptide is formed from radio-active L-a-amino-adipic acid, L-valine, and L-cysteine in P. chrysogenum and has the absolute configuration (159).153 Moreover, it has been shown to be a precursor for penicillin... 

The penicillins, from the fungus Penicillium chryso-genum, are the oldest and most widely used antibiotics. They are formed through stepwise build-up from a tripeptide (ACV) derived from a-Amino adipic acid, cysteine, and valine. Successive oxidation steps form the p-lactam and close the thiazolidine ring to form isopenicillin N. Action of an acyltransferase then yields penicillin G (Fig. 47). Alternatively, hydrolysis of isopenicillin N (or penicillin G) yields 6-aminopenicillanic acid, a key precursor for the wide range of semisynthetic pencillins used therapeutically. 

Substances related to MSG and purine 5 -ribonucleotides include peptides, amino acids (e.g. cysteine, homocysteine, cysteine S-sulfonic acid, aspartic acid, a-amino adipic acid, a-methyl glutamic acid, tricholomic acid, ibotenic acid), pyrrolidone carboxylic acid, 3-methyl thiopropyl amine, and others [2, 10], They are of less commercial interest than MSG, IMP, and GMP. Chemical structures of some of these substances are depicted in Fig. 3.53. Relative umami effects of some are shown in Tab. 3.49. Tricholomic acid and ibotenic acid have been found in the mushrooms Tricholoma muscarium and Amanita stroboliformis, respectively. 

Possibly formed by reaction of lysine and a-amino adipic acid 8-semi aldehyde... 

Formed from condensation of two a-amino adipic acid 8-semialdehyde residues... 

The numerous cross-linkages found in collagen are the result of the oxidation of lysine and hydroxylysine to a-amino adipic acid 8-semialde-hyde (allysine) and 8-hydroxy a-amino adipic acid 8-semialdehyde (hy-droxyallysine), respectively, following the assemblage of the collagen chains into the macromolecular structure (Equations 4 and 5) ... 

The cross-linkages found in collagen and elastin arise from the non-enzymatic interaction of a-amino adipic acid 8-semialdehyde (AL) and 8-hydroxy a-amino adipic acid 8-semialdehyde (HAL) with another residue of the aldehyde or with lysine, hydroxylysine, or histidine residues located at specific positions in the collagen polypeptide chains. Possible relationships among the different compounds in Table II are shown in Figures 4 and 5 for collagen and elastin. 

Thomas A. Perfetti, Ph.D. was born in 1952 in Jeannette, Pennsylvania, the second son of Ruth Peters and Bruno Massimo Perfetti. He was one of five children. Perfetti received his elementary education in several schools in the Pittsburgh area. In 1970, he entered Indiana University of Pennsylvania (lUP). He earned a Bachelor of Science degree in Chemistry in 1974. During his stay at lUP he conducted cell transport research with Dr. Richard Hartline and synthesized numerous radiopharmaceuticals. Perfetti s first publication was on the preferential uptake of t/-a-amino adipate by Alcaligens denitrificans in 1975. 

H.R.V. Amstein, D. Morris, The structure of a peptide containing a-amino-adipic add in the mycelium of Penicillium chyrsogenum. Biochem. J. 76 357-361 (1960)... 

Neurophysiologic and neuropharmacologic studies indicate that N-methy 1-Dr aspartic acid (NMD A) activates a distinct set of excitatory receptors that differ from those sensitive to either quisqualic acid or kainic acid. The excitatory effects of NMDA are selectively antagonized by the divalent cation Mg as well as by D-a-amino adipate and the more potent 2-amino-4-phosphonovaleric acid (Davies et al., 1979). Olney and co-workers (1971)... 

Figure 12.2 Lysine biosynthetic pathways. Six iysine biosynthetic pathways are discovered so far. a-amino adipate route (AAA) has two variants and Diaminopimeiate route (DAP) has four variants— Amino transferase pathway (Chlamydia), Succinyiase pathway (Gram-positive and Gram-negative bacteria), Acetyiase pathway (Bacillus), and Dehydrogenase pathway (Corynebacterium). in C. glutamicum succinyiase and dehydrogenase pathways are operated.

Homoserine also has been detected in filtrates of liver preparations incubated with methionine. Cantoni provisionally identified homoserine as a product of the acid hydrolysis of active methionine (S-adeno-sylmethionine). Beyond homoserine, the postulated reactions 2 and 3 are still more speculative. It might be presumed that homoserine is oxidized to aspartic acid, in analogy to the observations on the catabolism of lysine, in which the analogous a-amino adipic acid is an intermediate. If aspartic acid is formed, the subsequent reaction sequence is readily apparent. Evidence favorable to the proposed reaction pathway is the finding of Marshall and Friedberg, of the occurrence of a small amount of fumaric acid, labeled in the methine carbons, from the livers of mice injected with DL-methionine-2-C. ... 

In presence of transition metal cations and O2, a large number of phenolics exhibit also an amine oxidase-like activity (Akagawa Suyama, 2001). They convert lysine residues of proteins to a-amino-adipic semialdehyde residues. The oxidative deamination is initiated by the metal-catalyzed autooxidation of the phenolic compounds and by its reaction with the l,l-diphenyl-2-picryl hydrazyl (DPPH) radical, likely owing to the formation of quinine. But their biological significance and importance for plants remain to be understood. 

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