2.4- diaminobutyric acid

Fig. 7. Structure of one member of the amphomycin family where Dab = D-erythro-Oc, /5-diaminobutyric acid Dab = L-threo-a, /5-diaminobutyric acid ...

Ozonolysis of 5,8,9-trihydroxy-2,3-dihydro-l//-pyrimido[l, 2-n]quinoline-3-carboxylic acid (420), obtained from isopyoverdin isolated from Pseudomonas putida BTPl by acidic hydrolysis, gave l-2,4-diaminobutyric acid, which confirmed the hypothesis that heterocyclic chromophores 1 and 4 of pyoverdin and isopyoverdin, respectively, could have the same precursor, and the configuration at C(3) should be 5 (97ZN(C)549). 

C Ressler. Formation of a,Y-diaminobutyric acid from asparagine-containing peptides. J Am Chem Soc 78, 5956, 1956. 

Fig. 10. The mechanism of site-selective amidation of lysine residues in folded hehcal structures with His (i) Lys (i -t 4 or i-3) sites. The ester is typically p-nitrophenyl but can also be e.g. JV-hydroxysuccinimidyl. Ornithine and diaminobutyric acid residues will also be amidat-ed in the described positions...

Selenocystathionin occurs in seeds of the Central and South American Lecythis ollaria. It causes abdominal pain, nausea, vomiting, and diarrhea. Lathyrus odora-tus contains aminopropionitrile (Rosenthal and Bell, 1979). 2,4-Diaminobutyric acid (Fig. 11.10) in Lathyrus latifolius and Lathyrus sylvestris causes muscular weakness, paralysis, and death in humans and other mammals. In India, 25000 cases of this neurolathyrism were reported in a population of 634000 people (Rosenthal, 1991). 3-Cyanoalanine (Fig. 11.10) from Vivia sativa and 15 other Vivia species causes convulsion, rigidity, and death. 

Threonine and a,7-diaminobutyric acid are present within the structure of these antibiotics. The distinguishing feature of the polymyxine group is in that they contain 4-5 free / amine groups of a,7-diaminobutyric acid, which gives them the property of a cationic detergent able to form complexes with phospholipids of cellular membranes. All polymyxines are similar in term of antibiotic action. 

Diaminobutyric Acid.—a-7-Diaminobutyric acid was prepared in 1901 by E. Fischer by the same method as he employed in the synthesis of ornithine. 

Several 0-aminoacyl sugars were prepared to study a relationship between taste and chemical structure. Methyl a-D-glucopyranoside, methyl a-D-galactopyranoside and methyl a-D-mannopyranoside were selected as sugar skeletons. As basic amino acids, esters of lysine, ornithine, a,Y-diaminobutyric acid, and a,p-diaminopropionic acid were introduced into 2-0-, 3-0-, and 4-0- positions of sugars leaving only 6-hydroxyl group free. The results of sensory analysis are list in Table VI. O-... 

Several lines of investigation assert to the inability of canal ine to function as an effective ornithine antagonist. Ornithine interaction with canaline has been evaluated with the ornithine carbamoyl transferase (EC 2.1.3.3) of human liver. Neither canal ine nor ornithine inhibited this enzyme when the other member of this set served as the carbamoyl group recipient (29). The ornithine antagonist, 2,4-diaminobutyric acid drastically reduced urea production in the rat this reflected curtailment of the ornithine carbamoyl transferase-mediated conversion of ornithine to citrulline. Yet, canaline had no such effect on urea formation in this mammal (30). 

D Fouques, J Landry. Study of the conversion of asparagine and glutamine of proteins into diamino-propionic and diaminobutyric acids using [bis(trifluoroacetoxy)iodo]benzene prior to amino acid determination. Analyst 116 529-531, 1991. 

Polymyxin B Bacillus polymyxa R-Dab-Thr-Dab-Dab-Dab-(D) Phe-Leu-Dab-Dab-Thr (Dab is diaminobutyric acid) Cyclic lipopeptide 1.8 26 (59-61)... 

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