Mytilus synthesis

Hofmann, G.E., and G.N. Somero (1996a). Protein ubiquitination and stress protein synthesis in Mytilus trossulus occurs during recovery from tidal emersion. Mol. Mar. Biol. Biotech. 5 175-184. 

The isolation of azaspiracid-1 from poisonous mussels (Mytilus edulis) by Yasumoto and Satake was an admirable and Herculian accomplishment. Its originally proposed structure by these investigators stimulated considerable efforts to synthesize it in the laboratoiy. The efforts in om laboratory led first to the demise of the originally proposed structures and subsequently to the proposal and total synthesis of the correct structure of this fascinating natural product. 

Veldhuizen-Tsoerkan, M.B., Holwerda, D.A., van der Mast, C.A. and Zandee, D.I. (1991a) Synthesis of stress proteins under normal and heat shock conditions in gill tissue of sea mussels (Mytilus edulis) after chronic exposure to cadmium. Comp. Biochem. Physiol., 100C, 699-706. 

Williams and co-workers reported the non-enantioselective total syntheses of the heptacyclic indole alkaloids notoamide B (227) and stephacidin A (225) (Scheme 43) [168], and of their probable biogenetic precursor, notoamide C (213) (Scheme 41) [169]. The notoamides are fungal indole alkaloids from Aspergillus species collected fi-om the common mussel Mytilus edulis off Noto Island in the Sea of Japan [170, 171]. There is also a synthesis of the closely related notoamide J (217) (Scheme 42) [172]. 

The key reaction in the synthesis of biological organophosphates is the formation of a C-P linkage by the phosphoenolpyruvate phosphonopyruvate mutase reaction [Fig. 3(A)]. The enzyme has been purified from Tetrahymena pyriformis [35]. The equilibrium of the reaction is far on the side of phosphoenolpyruvate, and is shifted towards phosphonopyruvate formation by subsequent decarboxylation of phosphonopyruvate to phosphonoacetaldehyde [36]. Further phosphoenolpyruvate mutase enzymes have been characterized in Trypanosoma cruzi [37] and Mytilus edulis [38]. Phosphonoacetaldehyde is the key compound from which the synthesis of phosphonoethanolamine and phosphonomycin proceeds. Biosynthesis of phosphinothricin starts with an analogous reaction... 

Fig. 4. Mean ( S.E.) fractional rates of protein synthesis of the tissues of fasted Carcinus, at various times after feeding and of continuously fed animals. The animals were fed at time zero with Mytilus flesh at a ration level of 2.75% of the crab s live weight. The levels of significance from comparison with the fasted animals using Student s t-test are P < 0.05, P < 0.005, p < 0.001. (Data from Houlihan etal. 1990b)...

When the protein in the rations provided to each cod is compared with protein growth, synthesis and degradation a remarkable relationship between protein ingestion and protein synthesis appears (Fig. 10) for every gram of protein eaten, 1 g of protein was synthesised (Houlihan et al. 1989). Mytilus does not demonstrate this ratio between protein absorption and protein synthesis (Hawkins 1985) and it remains to be seen if the pattern will be repeated for other animals. However, the cod results raise the possibility that, as for rats, dietary protein, rather than energy, is the primary stimulus for muscle growth (Millward 1989). 

Fig. 20. a Results from the simultaneous measurements of oxygen consumption and whole body absolute rates of protein synthesis of cod made from starving animals and at various time points after feeding sand eels (Lyndon et al. unpubl.). b Relationship between mean absolute rates of protein synthesis and mean oxygen consumption for fasted, continuously fed and fasted crabs at 3, 9 and 16 h after a single meal. (Houlihan et al. 1990b) c Relationship between absolute rates of protein synthesis and oxygen consumption for Mytilus edulis (Hawkins et al. 1989)... 

Data from Mytilus using minimal theoretical costs suggest that protein synthesis accounts for approximately 20% of the heat loss at energy equilibrium (Hawkins et al. 1986,1989). These values are very similar to the proportions of the metabolic rate accounted for by protein synthesis using the same assumptions in a variety of mammals (e.g. Reeds et al. 1985). 

Haschemeyer AEV, Persell R, Smith MAK (1979) Effect of temperature on protein synthesis in fish of the Galapagos and Perlas Islands. Comp Biochem Physiol 64B 91-95 Hawkins AJS (1985) Relationships between the synthesis and breakdown of protein, dietary absorption and turnovers of nitrogen and carbon in the blue mussel, Mytilus edulis. Oecologia 66 42-49 Hawkins AJS, Bayne BL, Day AJ (1986) Protein turnover, physiological energetics and heterozygosity in the blue mussel, Mytilus edulis. the basis of variable age-specific growth. Proc R Soc (Lond) B 229 161-176... 

Mytilitol (C-methyl-scyllo-mositol) (66) (Fig. 1), m.p. 266-268°, is found in the muscle of Mytilus edvliSy a mussel (67) j and in a marine tunicate, Cionia intestinalis (68), The epimeric isomytilitol obtained synthetically through mi/o-inosose-2 (bioinosose) is 2-C-methyl-m2/o-inositol. Both pentaacetates and hexaacetates can be prepared from mytilitol presumably the tertiary hydroxyl resists acetylation. Postemak (66) has also succeeded in synthesizing hydroxymytilitol, m.p. 247°, and hydroxyiso-mytilitol, m.p. 233°, from m2/o-inosose-2 by means of the Amdt-Eistert synthesis. These are the first-known heptahydric homologs of an inositol. 

Macha, I.J., Ozyegin, L.S., Chou, J., Samur, R., Oktar, F.N., Ben-Nissan, B., 2013. An alternative synthesis method for dicalcium phosphate (monetite) powders from Mediterranean mussel (Mytilus galloprovincialis) shells. J. Aust. Ceram. Soc. 49 (2), 122-128. 

The development of a technology for the biological and chemical synthesis of analogs to the adhesive protein of the mussel Mytilus edulis is described. This protein consists mainly of the repeating decapeptide sequence Ala-Lys-Pro-Ser-Tyr-Hyp-Hyp-Thr-Tyr-Lys. 

Ishikawa, Y. and Nishiyama, S. (2004) Synthesis of the ABCD ring system of azaspiradd, a marine poison from Mytilus edulis. Heterocycles, 63, 885-893. 

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