Site selective oxidation of tricyclo[3.3.1.13,7]decane (adamantane) and some of its derivatives using fungi of the genus Absidia

Colin H. Ridyard, Roger A. Whittaker, Stanley D. Higgins, Stanley M. Roberts, Andrew J. Willets, Patrick D. Bailey, Georgina M. Rosair

Research output: Contribution to journalArticle

Abstract

Tricyclo[3.3.1.13,7]decane la has been converted into 1-hydroxytricyclo[3.3.1.13,7]decane 1b, tricyclo[3.3.1.1 3,7]decane-1,4ax-diol 4b, tricyclo[3.3.1.13,7]decane-1,3- diol 3b and to a lesser extent, 2-hydroxytricyclo[3.3.1.13,7]decane 4a (20 to 40% overall yield) using the microorganisms Absidia glauca (IMI 239693), A. cylindrospora (IMI 342950), A. spinosa (IMI 193887), A. spinosa var. biappendiculata (IMI 238610) and A. cylindrospora var. nigra (IMI 240053) as biocatalysts: In addition, A. cylindrospora (IMI 342950) converted tricyclo[3.3.1.13,7]decane-1-carboxylic acid 1c into 4ax-hydroxytricyclo[3.3.1.13,7]decane-1-carboxylic acid 4c with almost complete regioselectivity. Tricyclo[3.3.1.13,7]decane derivatives 1d-g were used as biohydroxylation substrates with A. cylindrospora (IMI 342950), giving selective biohydroxylation at the 4ax- and/or the 3-position. The 4ax-selectivity was confirmed by X-ray crystal structure determinations of 4b, 4c and 4j.

Original languageEnglish
Pages (from-to)1811-1819
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 2
Volume9
DOIs
Publication statusPublished - Sep 1996

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Adamantane
Fungi
Derivatives
Oxidation
Carboxylic Acids
Regioselectivity
decane
Microorganisms
Crystal structure
X rays
Substrates
Enzymes

Cite this

Ridyard, Colin H. ; Whittaker, Roger A. ; Higgins, Stanley D. ; Roberts, Stanley M. ; Willets, Andrew J. ; Bailey, Patrick D. ; Rosair, Georgina M. / Site selective oxidation of tricyclo[3.3.1.13,7]decane (adamantane) and some of its derivatives using fungi of the genus Absidia. In: Journal of the Chemical Society, Perkin Transactions 2. 1996 ; Vol. 9. pp. 1811-1819.
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abstract = "Tricyclo[3.3.1.13,7]decane la has been converted into 1-hydroxytricyclo[3.3.1.13,7]decane 1b, tricyclo[3.3.1.1 3,7]decane-1,4ax-diol 4b, tricyclo[3.3.1.13,7]decane-1,3- diol 3b and to a lesser extent, 2-hydroxytricyclo[3.3.1.13,7]decane 4a (20 to 40{\%} overall yield) using the microorganisms Absidia glauca (IMI 239693), A. cylindrospora (IMI 342950), A. spinosa (IMI 193887), A. spinosa var. biappendiculata (IMI 238610) and A. cylindrospora var. nigra (IMI 240053) as biocatalysts: In addition, A. cylindrospora (IMI 342950) converted tricyclo[3.3.1.13,7]decane-1-carboxylic acid 1c into 4ax-hydroxytricyclo[3.3.1.13,7]decane-1-carboxylic acid 4c with almost complete regioselectivity. Tricyclo[3.3.1.13,7]decane derivatives 1d-g were used as biohydroxylation substrates with A. cylindrospora (IMI 342950), giving selective biohydroxylation at the 4ax- and/or the 3-position. The 4ax-selectivity was confirmed by X-ray crystal structure determinations of 4b, 4c and 4j.",
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Site selective oxidation of tricyclo[3.3.1.13,7]decane (adamantane) and some of its derivatives using fungi of the genus Absidia. / Ridyard, Colin H.; Whittaker, Roger A.; Higgins, Stanley D.; Roberts, Stanley M.; Willets, Andrew J.; Bailey, Patrick D.; Rosair, Georgina M.

In: Journal of the Chemical Society, Perkin Transactions 2, Vol. 9, 09.1996, p. 1811-1819.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Site selective oxidation of tricyclo[3.3.1.13,7]decane (adamantane) and some of its derivatives using fungi of the genus Absidia

AU - Ridyard, Colin H.

AU - Whittaker, Roger A.

AU - Higgins, Stanley D.

AU - Roberts, Stanley M.

AU - Willets, Andrew J.

AU - Bailey, Patrick D.

AU - Rosair, Georgina M.

PY - 1996/9

Y1 - 1996/9

N2 - Tricyclo[3.3.1.13,7]decane la has been converted into 1-hydroxytricyclo[3.3.1.13,7]decane 1b, tricyclo[3.3.1.1 3,7]decane-1,4ax-diol 4b, tricyclo[3.3.1.13,7]decane-1,3- diol 3b and to a lesser extent, 2-hydroxytricyclo[3.3.1.13,7]decane 4a (20 to 40% overall yield) using the microorganisms Absidia glauca (IMI 239693), A. cylindrospora (IMI 342950), A. spinosa (IMI 193887), A. spinosa var. biappendiculata (IMI 238610) and A. cylindrospora var. nigra (IMI 240053) as biocatalysts: In addition, A. cylindrospora (IMI 342950) converted tricyclo[3.3.1.13,7]decane-1-carboxylic acid 1c into 4ax-hydroxytricyclo[3.3.1.13,7]decane-1-carboxylic acid 4c with almost complete regioselectivity. Tricyclo[3.3.1.13,7]decane derivatives 1d-g were used as biohydroxylation substrates with A. cylindrospora (IMI 342950), giving selective biohydroxylation at the 4ax- and/or the 3-position. The 4ax-selectivity was confirmed by X-ray crystal structure determinations of 4b, 4c and 4j.

AB - Tricyclo[3.3.1.13,7]decane la has been converted into 1-hydroxytricyclo[3.3.1.13,7]decane 1b, tricyclo[3.3.1.1 3,7]decane-1,4ax-diol 4b, tricyclo[3.3.1.13,7]decane-1,3- diol 3b and to a lesser extent, 2-hydroxytricyclo[3.3.1.13,7]decane 4a (20 to 40% overall yield) using the microorganisms Absidia glauca (IMI 239693), A. cylindrospora (IMI 342950), A. spinosa (IMI 193887), A. spinosa var. biappendiculata (IMI 238610) and A. cylindrospora var. nigra (IMI 240053) as biocatalysts: In addition, A. cylindrospora (IMI 342950) converted tricyclo[3.3.1.13,7]decane-1-carboxylic acid 1c into 4ax-hydroxytricyclo[3.3.1.13,7]decane-1-carboxylic acid 4c with almost complete regioselectivity. Tricyclo[3.3.1.13,7]decane derivatives 1d-g were used as biohydroxylation substrates with A. cylindrospora (IMI 342950), giving selective biohydroxylation at the 4ax- and/or the 3-position. The 4ax-selectivity was confirmed by X-ray crystal structure determinations of 4b, 4c and 4j.

U2 - 10.1039/P29960001811

DO - 10.1039/P29960001811

M3 - Article

VL - 9

SP - 1811

EP - 1819

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

SN - 0300-9580

ER -