Synthesis of DL-3,5-Dihydroxy-3-methylpentanoic Acid (Mevalonic Acid)

Hoffman, Carl H.; Wagner, Arthur F.; Wilson, Andrew; Walton, Edward; Shunk, Clifford H.; Wolf, Donald E.; Holly, Frederick W.; Folkers, Karl

doi:10.1021/ja01566a080

Cited by 64 publications

(20 citation statements)

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“…2 carbanion source and a C 4 unit 4 unit such as 4-bromoacetate. [14][15][16][17] reactions have been developed based on the lithium carbanion derived from acetic acid. 18 Full experimental details for this procedure are given in ref.…”

Section: Carbon-labelled Mevalonatesmentioning

confidence: 99%

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Fifty Years of the Synthesis of Labelled Mevalonic Acid

Hanson

2008

Journal of Chemical Research

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Section: Carbon-labelled Mevalonatesmentioning

confidence: 99%

“…The original trivial 4 3 rat liver homogenates. [2- 14 C]Mevalonolactone, (±)-2 14 C]bromoacetate 4 5 and found to 1,2 In 1957, [5][6][7] it the C 5 6 mevalonic acid.…”

mentioning

confidence: 99%

Fifty Years of the Synthesis of Labelled Mevalonic Acid

Hanson

2008

Journal of Chemical Research

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“…The supernatant fluid was concentrated to dryness in vacuo (Anderson and Porter, 1962). The dibenzylethylene diamine salt of mevalonic acid was formed by the method of Hoffman et al (1957) and recrystallized to constant specific activity.…”

Section: Mevalonic Acid In Mycoplasmamentioning

confidence: 99%

Comparative Biosynthesis of Mevalonic Acid by Mycoplasma

Smith

Henrikson

1965

J Bacteriol

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SMITH, PAUL F. (University of South Dakota, Vermillion), AND C. A". HENRIKSON. Comparative biosynthesis of mevalonic acid by Mycoplasma. J. Bacteriol. 89:146-153. 1965.-Three representative Mycoplasma, M. laidlawii strain B, M. gallisepticum strain J, and M. hominis strain 07, were examined for the presence or absence of enzymes associated with the biosynthetic pathway to mevalonic acid. M. laidlawii served as a control, because it synthesizes carotenoids from acetate. M. laidlawii was shown to contain a specific acetokinase and phosphotransacetylase for the synthesis of acetyl coenzyme A, and a ,3-ketothiolase and coenzyme A transferase for the synthesis of acetoacetyl coenzyme A. M. gallisepticum contained a specific acetokinase, phosphotransacetylase, and possibly an aceto coenzyme A kinase forming acetyl coenzyme A; it also contained a B-ketothiolase, a coenzyme A transferase, and a coenzyme A transphorase forming acetoacetyl coenzyme A directly or indirectly. The B-ketothiolase of M. gallisepticum was not affected by iodoacetamide, in contrast to the other two strains. M. laidlawii exhibited ,B-hydroxy-,B-methylglutaryl coenzyme A condensing enzyme, and M. hominis did not. This activity of M. gallisepticum was masked by thiolase activity. II1. laidlawii and M. gallisepticum contained a nicotinamide adenine dinucleotide phosphate-linked ,B-hydroxy-3-methylglutaryl coenzyme A reductase, and M. hominis did not. C14labeled acetate was incorporated into mevalonic acid only by M. laidlawii and M. gallisepticuni. The lack of fl-hydroxy-f#-methylglutaryl coenzyme A condensing enzyme and reductase activities in M. hominis explains its growth requirement for sterol. The enzymatic block in M. gallisepticum must occur after mevalonic acid in the biosynthetic pathway to terpenoids.

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“…Although a number of methods for the synthesis of isotopically labelled mevalonic acid lactone (1) have been described in recent years,'-' there are a few applicable to the synthesis of the 3'-and/or 3-labelled compounds. A short, high yielding synthesis of mevalonic acid lactone which enabled isotopic labels to be introduced into these positions was recently described.…”

mentioning

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Studies on a synthesis of (RS)-mevalonic acid lactone

Bardshiri¹,

Simpson²,

Scott³

et al. 1984

J. Chem. Soc., Perkin Trans. 1

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Full details of a high yielding synthesis of mevalonic acid lactone (1) which is of particular value in the preparation of 3and/or 3'-labelled compounds are described. The key step, conversion of 3hydroxy-3-methylpentane-I ,5-dioic acid (3) into 3hydroxy-3-methylpentane-I ,5-dioic anhydride (4) using acetic anhydride, has been fully investigated, and an additional method using acetyl chloride and triethylamine is described.

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Synthesis of DL-3,5-Dihydroxy-3-methylpentanoic Acid (Mevalonic Acid)

Cited by 64 publications

References 0 publications

Fifty Years of the Synthesis of Labelled Mevalonic Acid

Fifty Years of the Synthesis of Labelled Mevalonic Acid

Comparative Biosynthesis of Mevalonic Acid by Mycoplasma

Studies on a synthesis of (RS)-mevalonic acid lactone

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