The hydroxylation of globulol and 7-epiglobulol by Cephalosporium aphidicola

Hanson, James R.; Hitchcock, Peter B.; Manickavasagar, Revathy

doi:10.1016/s0031-9422(00)89521-7

Cited by 12 publications

(9 citation statements)

References 9 publications

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“…Diplodia gossypina, 5 Cephalosporium aphidicola 6 and Glomerella cingulata 7 has been reported previously and we now report the action of Mucor plumbeus, an organism that has been widely used for biotransformation.…”

supporting

confidence: 61%

Hydroxylation of Aromadendrane Derivatives by Mucor plumbeus†

Guillermo¹,

Hanson²,

Truneh³

1997

J. Chem. Res.

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supporting

confidence: 61%

Hydroxylation of Aromadendrane Derivatives by Mucor plumbeus†

Guillermo¹,

Hanson²,

Truneh³

1997

J. Chem. Res.

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“…These include Botrytis cinerea [20], Cephalosporium aphidicola [21], Glomerela cingulata [22] and a number of other organisms [23]. It is apparent from these results that a similar analysis can lead to predictive models for these organisms.…”

Section: Other Sesquiterpenoid Microbial Hy-droxylationsmentioning

confidence: 95%

The Biotransformation of Sesquiterpenoids by Mucor plumbeus

Arantes¹,

Hanson²

2007

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The regiospecificity of the microbiological hydroxylation of sesquiterpenoids by the fungus, Mucor plumbeus is reviewed. It is shown to fit a pattern which can be rationalized in terms of a model. INTRODUCTIONBiotransformations can provide economical and environmentally friendly means of carrying out reactions with a regio-and stereospecificity that can sometimes complement that of chemical methods. Amongst these methods, microbiological hydroxylations constitute powerful synthetic tools for substitution at centres that are often otherwise chemically inert. These biohydroxylations may have a high regioselectivity and they can proceed without the use of protecting groups under fermentation conditions which are chemically mild. The method has been reviewed on many occasions and is the subject of several books [1]. However these reviews have tended to concentrate on groups of substrates such as steroids [2], sesquiterpenoids [3] and diterpenoids [4] and the products of biotransformation by several organisms rather than addressing the capabilities of particular organisms. If an organism is to be considered for general preparative use, a predictive model of its capabilities is required.In order to overcome difficulties associated with factor regeneration and the isolation of potentially sensitive enzyme systems, intact organisms are commonly used for microbiological hydroxylation. The application of microbiological hydroxylation is limited by a shortage of predictive models for particular organisms. Such models have the obvious limitations that they are constructed in terms of the whole organism even though more than one hydroxylase may be present. Nevertheless useful information on the steric relationships which exist between polar groups in a substrate and the site of hydroxylation has accrued from the study of steroid transformations. Some models have been proposed as a consequence of this work [5]. However the steroids are relatively flat and hence there is a limit to the extent to which they can probe the three-dimensional geometry of the active site. Despite these limitations it is possible to predict the likely sites of microbiological hydroxylation of a steroid by a particular organism.Mucor species are common saprophytic fungi which grow on a variety of materials suggesting that they may be capable of transforming a range of different substrates, i.e. they are potentially useful organisms for microbiological transformations. A number have been used for this purpose, including Mucor plumbeus which is the subject of this review.

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“…The former is useful for the hydroxylation of various substrates including monoterpenes (Atta-ur-Rahman et al 1998), diterpenoids (Takahashi et al 2000), sesquiterpenes (Hanson et al 1994) and steroids (Fernandes et al 2003, Kiran et al 2004b. To our knowledge the biotransformation of racemic diisophorone by N. crassa is the first report on the biotransformation ability of this fungus on sesquiterpene type structures.…”

Section: Introductionmentioning

confidence: 98%