Three‐dimensional structure of monoanionic methionine‐enkephalin: X‐ray structure of tert‐butyloxycarbonyl‐Tyr‐Gly‐Gly‐(4‐bromo)Phe‐Met‐OH
Mitsunobu DoiToshimasa IshidaMasatoshi InoueT. FujiwaraKen‐ichi TomitaTerutoshi KimuraShunpei Sakakibara
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Abstract:
The conformation of tert ‐butyloxycarbonyl‐Tyr‐Gly‐Gly‐(4‐bromo)Phe‐Met‐OH, as a monoanionic derivative of Met‐enkephalin, was elucidated by X‐ray crystal analysis. The molecule took an extended conformation which was bended at the Phe residue. The implication of the dimer formation caused by 4 intermolecular hydrogen bonds was discussed in the relation with the opiate receptor.Keywords:
Residue (chemistry)
Derivative (finance)
Summary. This paper reports the results of growth tests on young white rats on diets adequate in other respects but containing varying concentrations of L‐ and D‐methionine. The following results were obtained: The concentration required for maintenance of the body‐weight was 0.10 % L‐methionine and 0.12 % D‐methionine in the diet. The effect of the D‐methionine on the growth was merely 76–84 per cent, of that of the L‐methionine. Maximal growth was obtained at a concentration of 0.25–1% L‐methionine and of 0.5C–.2% D‐methionine in the diet. D‐methionine seems to be less toxic than L‐methionine. A toxic effect on the growth (stagnation in weight) resulted at a concentration of 3.5% L‐methionine and of 5.4% D‐methionine in the diet. In default of methionine in the diet the animals had a poor appetite, which immediately improved on the addition of L‐ or D‐methionine. A maximal appetite was obtained with 0.125–1% L‐methionine or 0.125–4% D‐methionine. With higher concentrations a decrease in appetite would appear.
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Intermolecular interaction
Blueshift
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Methionine synthase
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Methionine synthase
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Soybean [ Glycine max (L.) Merr.] protein, which is deficient in the sulfur amino acids, especially methionine, is consumed world‐wide by both humans and other animals. Methionine deficiency is caused by an abundance of the β‐chain of β‐conglycinin, a seed storage protein that lacks methionine. De novo synthesis of the β‐chain is inhibited by an elevated concentration of methionine. The objectives of our investigations were to mutagenize soybean seeds, characterize a methionine over‐producing phenotype, and select several methionine over‐producing genetic lines. Mutant lines with a methionine over‐producing phenotype were isolated and crossed. Seeds from a cross, designated H82 × 20a 2 , contained a normal seed nitrogen concentration and an 18% increase in seed sulfur concentration. The S/N atomic ratio of line H82 × 20a 2 was 16.2% greater than that of the parental line. Amino acid analyses of seeds from the derived and parental lines revealed mole percentages of 1.84 and 1.51, respectively, for methionine and 1.685 and 1.32, respectively, for cysteine. Thus, seed methionine and cysteine concentrations of H82 × 20a 2 were each approximately 20% greater than those of the parental line. Protein produced by the derived line may fulfill nutritional requirements for methionine and cysteine.
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Cooper, Stephen (University Institute of Microbiology, Copenhagen, Denmark). Utilization of d -methionine by Escherichia coli . J. Bacteriol. 92: 328–332. 1966.—Methionine-requiring strains of Escherichia coli grow on d -methionine. Mutants can be isolated which cannot grow on d -methionine. The d -methionine nonutilizing mutation is independent of the methionine requirement, and maps near the lac region of the E. coli genome. Growth of methionine-requiring strains on d -methionine is dependent upon aerobic conditions. Cells grown on d -methionine have a sixfold greater ability to incorporate d -methionine into protein than cells grown on l -methionine. The incorporation of d -methionine is inhibited by l -methionine.
Methionine synthase
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Methionine-dependence is a tumor-specific biochemical defect expressed by the inability or decreased ability of tumors to grow under the condition of methionine-depletion. Many reports have shown that methionine-dependence occurs in human tumors of all types, including fresh surgical specimens in vitro. However, in vivo determinations of methionine-dependence have thus far been made only in rodent malignant tumors using methionine-deficient diets. We report here for the first time that human cancer xenografts in nude mice are methionine-dependent and when fed a methionine-free diet tumor growth is greatly inhibited. The body weight of mice on the methionine-free diet was found to be maintainable by once-per-week administration of methionine. The data presented here suggest that methionine-dependence can be an important target for human cancer treatment.
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Rats and chickens, unlike man, utilize D-methionine efficiently. We have studied urinary excretion of methionine isomers in young miniature pigs, adult rabbits, and adult dogs given D-methionine in an attempt to find an animal model that, like man, utilizes the D-isomer poorly. Six-week-old miniature pigs ingesting a protein-free diet were infused with 8.5% amino acid solutions differing only in methionine isomer content (L- vs DL-) to supply amino acid requirements. Each solution was infused for a 2- or 3-day period in a cross-over design. Plasma methionine levels were significantly higher (p = 0.01) during infusion of the solution providing DL-methionine, with 25% of total plasma methionine present as the D-configuration. However, urinary methionine excretion was similar with both solutions, with D-methionine utilization calculated as greater than 99%. Adult rabbits ingesting DL-methionine (0.14 g/100 g food) showed good utilization of D-methionine, excreting less than 1.3% D-isomer in the urine. Mixed breed dogs given 1.25 g D-methionine in their drinking water excreted less than 0.4% of ingested D-methionine in the urine. These data indicate that the pig, rabbit, and dog utilize D-methionine efficiently, behaving like the rat and chicken rather than man.
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IT HAS been demonstrated by many workers (Bird and Mattingly, 1945; Clandinin et al., 1946; Saxena and McGinnis, 1952; German and Couch, 1950; and others) that the addition of methionine to broiler rations accelerated growth. Marett and Sunde (1966) found that full utilization of the isomers of methionine by the chick was dependent on the amino acid composition of the diets. The incorporation of methionine analogue did not produce as great a growth as did l-methionine. The results indicated that when mixtures of l-methionine and methionine analogue were supplemented to the diet of chicks at levels, equivalent to a 0.5% and 0.7% l-methionine, mixtures of about ⅔ l-methionine and ⅓ methionine analogue produced growth significantly better than with methionine analogue alone, ⅔ methionine analogue or ½ l-methionine mixtures. The above workers also found that when l-methionine was used at 0.8% level and compared with 0.96% methionine analogue (0.08% l-methionine equivalent), . . .
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