Professor Derek Boyd

Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols, D. R. Boyd, N. D. Sharma, J. F. Malone, P. B. A. McIntyre, P. J. Stevenson, C. McRoberts, J. Gawronski, M. Kwit and C. C. R. Allen, Org. Biomol. Chem., 2012, Advance Article DOI: 10.1039/C2OB25079A

Chemoenzymatic synthesis of (-)-epibatidine, D. R. Boyd, N. D. Sharma, M. Kaik, M. Bell, P. B.A McIntyre, B. Kelly, P. J. Stevenson and C.C. R. Allen,Org. Biomol. Chem, 2012, 10, 2774-2779.

Chemoenzymatic synthesis of a mixed phosphine-phosphine oxide organocatalyst and its application to the asymmetric allylation of aldehydes and hydrogenation of alkenes, M. Bell, D. R. Boyd, K. S. Dunne, J. F. Malone, B. Kelly, P. J. Stevenson, Org. Biomol. Chem., 2012, 10, 1388-1395.

Bacterial mono- and di-oxygenase-catalysed heteroatom oxidation of benzo[b]thiophenes and related compounds, D. R. Boyd, N. D. Sharma, N. S. A. Haughey, B. McMurray, J. F. Malone, C. C. R. Allen and K. O'Connor, L. Coumelen , Org. Biomol. Chem., 2012, 10, 782-790.

Acid-catalysed dehydration of naphthalene-cis-1,2-dihydrodiols: origin of impaired resonance effects of 3-substituents, J. S. Kudavalli, D. R. Boyd, N. D. Sharma and R. A. More O'Ferrall, J. Org. Chem., 2011, 76, 9338-9343.

Hyperaromatic stabilization of arenium ions: remarkable cis stereoselectivity of nucleophilic trapping of β-hydroxyarenium ions by water. D. A. Lawlor, J. Kudavalli, A. C. MacCormac, D. A. Coyne, D. R. Boyd and R. A. More O'Ferrall, J. Am. Chem. Soc., 2011, 133, 19718-19728.

Cycloalkenyl halide substitution reactions of enantiopure arene cis-tetrahydrodiols with boron, nitrogen and phosphorus nucleophiles, D. R. Boyd, N. D. Sharma, M. Kaik, M. Bell, M. V. Berberian, P. B.A McIntyre, B. Kelly, C. Hardacre, P. J. Stevenson and C.C. R. Allen, Adv. Synth. Catal., 2011, 353, 2455-2465.

Dioxygenase-catalysed cis-dihydroxylation of phenols to yield cyclohexenone cis-diols and related metabolites, D. R. Boyd, N. D. Sharma, P. Stevenson, C. McRoberts, J. T. G. Hamilton, J. M. Argudo, H. Mundi, L. A. Kulakov and C. C. R. Allen, Org. Biomol.Chem., 2011, 9, 1479-1490.

Chemoenzymatic synthesis of carbasugars (+)-pericosines A-C from diverse aromatic cis-dihydrodiol precursors, D. R. Boyd, N. D. Sharma, C. Acaru, J. F. Malone, C. R. O'Dowd, C. C. R. Allen, P. J. Stevenson, Org. Lett. 2010, 12, 2206-2209.

Circular dichroism, optical rotation and absolute configuration of 2-cyclohexenone cis-diol type phenol metabolites: Redefining the role of substituents and 2-cyclohexenone conformation in electronic circular dichroism spectra, M. Kwit, J. Gawronski, D. R. Boyd, N. D. Sharma and M. Kaik, Org. Biomol.. Chem., 2010, 8, 5635-5645.

Hyperaromatic stabilisation of arenium Ions, J. S. Kudavalli, D. R.Boyd, D. Coyne, J. R. Keeffe, D. A. Lawlor, A. C. McCormack, R. A. More O'Ferrall, S. N. Rao and N. D. Sharma, Org.Lett. 2010, 12, 5550-5553.

Synthesis and reactions of enantiopure substituted benzene cis-hexahydrodiols, D. R. Boyd, N. D. Sharma, M. V. Berberian, K. Dunne, C. Hardacre, M. Kaik, B. Kelly, J. F. Malone, S. T. McGregor, P. J. Stevenson, Adv. Synth. Catal., 2010, 352, 855-868.

Chemoenzymatic synthesis of the carbasugars carba-β-L-galactopyranose, carba-β-L-talopyranose and carba-α-L-talopyranose from methylbenzoate, D. R. Boyd, N. D. Sharma, N. I. Bowers, G. P. Coen, J. F. Malone, C. R. O’Dowd, P. Stevenson, and C. C. R. Allen, Org. Biomol.Chem., 2010, 8, 1415-1423.

Chemoenzymatic synthesis of chiral 2,2'-bipyridine ligands and their N-oxide derivatives: applications in the asymmetric aminolysis of epoxides and asymmetric allylation of aldehydes, D. R. Boyd, N. D. Sharma, L. Sbircea, D. Murphy, J. F. Malone, S. L. James, C. C. R. Allen and J. T. G. Hamilton, Org. Biomol. Chem., 2010, 8, 1081-1090.

Circular dichroism spectra, optical rotations and absolute configurations of cis-dihydrodiol metabolites of quinoline and derivatives: the role of the nitrogen atom, M. Kwit, J. Gawronski, L. Sbircea, N. D. Sharma, M. Kaik, D. R. Boyd, Chirality, 2009, 21, S37-S47.

New families of enantiopure cyclohexenone-cis-diol, o-quinol dimer and hydrate metabolites from dioxygenase-catalysed dihydroxyaltion of phenols, N. D. Sharma, C. C. R. Allen, J. F. Malone , D. R. Boyd, Chem. Commun. 2009, 3633-3635.

Synthesis and absoloute configuration assignments of mono- and di-substituted chiral quinoline alkaloids by asymmetric oxidation, D. R. Boyd, N. D. Sharma, S. A. Barr and P. L. Loke, Heterocycles, 2009, 79, 831-850.

Toluene dioxygenase-catalysed synthesis of cis-dihydrodiol metabolites from 2- substituted naphthalene substrates: absolute configurational and conformational assignments based on circular dichroism and optical rotation measurements, M. Kwit, J. Gawronski, D.R. Boyd, N. D. Sharma, M. Keik, R. A. More O’Ferrall and J. S. Kudavalli, Chem. Eur. J. , 2008, 14, 11500-11511.

Chemoenzymatic synthesis of chiral 4,4'-bipyridyls and their metal organic frameworks, L. Sbircea, N. D. Sharma, W. Clegg, R. W. Harrington, P.N. Horton, M.B. Hursthouse, D.C. Appelby, D.R. Boyd and S.L. James, Chem. Commun., 2008, 5539-5541.

Azaarene cis-dihydrodiols: applications in new chemoenzymatic routes to 2,2'-bipyridine ligands for catalytic asymmetric allylic oxidations and cyclopropanations, D.R. Boyd, N.D. Sharma, L. Sbircea, D. Murphy, T. Belhocine, J.F. Malone, S.L. James, C.C.R. Allen and J.T.G. Hamilton, Chem. Commun., 2008, 5535-5537.

Regioselectivity and steroeselectivity of dioxygenase-catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates, D.R. Boyd, N.D. Sharma, G.P. Coen, F. Hempenstall, Vera Ljubez, J.F.Malone, C.C.R. Allen and J.T.G. Hamilton, Org.Biomol.Chem., 2008, 3957-3966

Enzyme-catalysed synthesis and reactions of benzene oxide/oxepine derivatives of methyl benzoates, D.R. Boyd, N.D. Sharma, J.S. Harrison, J.F. Malone, W.C. McRoberts, J.T.G. Hamilton and D.B. Harper, Org.Biomol.Chem., 2008, 6, 1251-1259.

Determination of absolute configuration of conformationally flexible cis-dihydrodiol metabolites:effect of diene substitution pattern on the circular dichroism spectra and optical rotations, M. Kwit, N.D. Sharma, D.R. Boyd, J. Gawronski, Chirality, 2008, 20, 609-620.

Tandem enzyme-catalysed reduction / cis-dihydroxylation of 2,2,2- trifluoroacetophenone: chemoenzymatic routes to enantiopure phenols and trans-dihydrodiols, D.R. Boyd, N.D. Sharma, V. Ljubez, J.F. Malone, C.C.R. Allen, J Chem Tech Biotechnol, 2007, 82, 1072-1081 

Synthesis, structure and stereochemistry of quinoline alkaloids resulting from enzyme-catalysed oxidation pathways in Choisya ternata, D. R. Boyd, N. D. Sharma, P.L. Loke, J. F. Malone, W. C. McRoberts and J.T.G. Hamilton, Org. Biomol.Chem., 2007, 5, 2983-2991. 

Syn-Benzene dioxides: chemoenzymatic synthesis from cis-2,3-dihydrodiol derivatives of monosubstituted benzenes and threir application in the synthesis of regioisomeric 1,2- and 3,4-cis-dihydrodiols and 1,4-dioxocins, D.R. Boyd, N.D. Sharma, N.M. Llamas, C.R. O’Dowd,and C.C.R. Allen, Org.Biomol.Chem., 2007, 5, 2267-2273.

Enzyme-catalysed synthesis and absolute configuration assignments of cis- dihydrodiol metabolites from 1,4-disubstituted benzenes , D.R. Boyd, N.D. Sharma, G.N. Coen, P. Gray, J.F. Malone, J. Gawronski Chem. Eur. J. , 2007, 13, 5804-5811.

Absolute configuration of conformationally flexible cis-dihydrodiol metabolites by the method of confrontation of experimental and calculated ECD spectra and optical rotations, M. Kwit, N.D. Sharma, D.R. Boyd, J. Gawronski Chem. Eur. J. , 2007, 13, 5812-5821.

Syn-Benzene dioxides: chemoenzymatic synthesis from cis-2,3-dihydrodiol derivatives of monosubstituted benzenes and thrie application in the synthesis of regioisomeric 1,2- and 3,4-cis-dihydrodiols and 1,4-dioxocins.D.R. Boyd, N.D. Sharma, N.M. Llamas, C.R. O'Dowd,and C.C.R. Allen, Org. Biomol. Chem., 2007, 5, 2267-2273.

A comparative study of enzymatic and chemo-enzymatic routes for the synthesis of 3-substituted catechols, V. Berberian, C.C.R. Allen, N.D. Sharma, D.R. Boyd, C. Hardacre, Adv. Synth. Catal., 2007, 349, 727-739

Chemoenzymatic synthesis of the trans-2,3-dihydrodiol derivatives of monosubstituted benzenes from the corresponding cis-2,3-dihydrodiol isomers D.R. Boyd, N.D. Sharma, G.P. Coen, V. Ljubez, P. K. M. McGeehin, C.C.R. Allen, Org. Biomol. Chem., 2007, 514-522

Dioxygenase-catalysed dihydroxylation of arene cis-dihydrodiols and acetonide derivatives: a new approach to the synthesis of enantiopure tetraoxygenated arene bioproducts, D.R. Boyd, N.D. Sharma, T. Belhocine, P.L. Loke, J.F. Malone, S. McGregor, C.C.R. Allen, J. Chem. Soc., Chem. Commun., 2006, 4934-4936.

Dioxygenase-catalysed oxidation of disubstituted benzene substrates; benzylic hydroxylation versus aryl dihydroxylation and evidence for for a meta effect. D.R. Boyd, N.D. Sharma, N.I. Bowers, H. Dalton, M.D. Garrett, J.S. Harrison, G.N. Sheldrake, Org. Biomol. Chem., 2006, 4, 3343-3349.

Chemoenzymatic synthesis of the trans-dihydrodiol isomers of monosubstituted benzenes via anti-benzene dioxides,.D.R. Boyd, N.D. Sharma, N.M. Llamas, C.R. O'Dowd,and C.C.R. Allen, Org. Biomol. Chem., 2006, 4, 2208-2217.

Arene diol formation: from biology to application, D.R. Boyd and T. Bugg, Perspective Article, Org. Biomol. Chem., 2006, 4, 181-192.

cis-Dihydrodiol, arene oxide and phenol metabolites of dictamnine: key intermediates in the biodegradation and biosynthesis of furoquinoline alkaloids. D.R. Boyd, N.D. Sharma, C. O'Dowd, J.G Carroll, P.L. Loke, and C.C.R. Allen, J. Chem. Soc., Chem. Commun, 2005, 3989-3991.

Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cyclic cis-Diols, D.R. Boyd, N.D. Sharma, I.N. Brannigan, M.R. Groocock, J.F.Malone, G. McConville, C.C.R. Allen, Adv. Synth. Catal., 2005, 347, 1081-1089.

Chemoenzymatic synthesis of carbasugars from iodobenzene, D.R. Boyd, N.D. Sharma, N. Llamas, J.F. Malone, C.R. O’Dowd, C.C.R. Allen, Org. Biomol.Chem., 2005, 3, 1953-1963.

Absolute configuration, conformation and circular dichroism of monocyclic arene dihydrodiol metabolites:it is all due to the heteroatom substituents, D.R. Boyd, A. Drake, J Gawronski, M. Kwit, J. F. Malone and N.D. Sharma, J. Am. Chem. Soc, 2005, 127, 4308-4309.

Dioxygenase-catalysed oxidation of alkylaryl sulfides; sulfoxidation versus dihydrodiol formation, D.R. Boyd, N.D. Sharma, A. King,B. Byrne, S.A. Haughey, M.A. Kennedy, C.C.R. Allen,Org. Biomol. Chem., 2004, 2, 2530-2537.

Isolation and characterisation of bacterial strains containing enantioselective DMSO reductase activity: application to the kinetic resolution of racemic sulfoxides, H.R. Luckarift, H. Dalton, N.D. Sharma, D.R. Boyd, and R.A. Holt, Applied Microbiology and Biotechnology, 2004, 65, 678-685.

Stereoselective reductase-catalysed deoxygenation of sulfoxides in aerobic and anaerobic bacteria, D.R. Boyd, N.D. Sharma, A. King, S.D. Shepherd, C.R. Allen, R. Holt, H. Luckarift and H. Dalton, Org. Biomol. Chem., 2004, 2,554.

Dioxygenase-catalysed sulfoxidation of bicyclic alkylaryl sulfides and chemoenzymatic synthesis of acyclic disulfoxides, D.R. Boyd, N.D. Sharma, S. Haughey, M.A. Kennedy, J.F. Malone, S. Shepherd, C.C.R. Allen and Howard Dalton, Tetrahedron., 2004, 60, 549.

Stereochemical and mechanistic aspects of dioxygenase-catalysed benzylic hydroxylation, D.R. Boyd, N.D. Sharma, N.I. Bowers, R. Boyle, J.S. Harrison, K. Lee and D.T. Gibson, Org. Biomol. Chem., 2003, 1, 1298-1307.

Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. D.R. Boyd, N.D. Sharma, N. Gunaratne, S.A. Haughey, M.A. Kennedy, J.F. Malone, C.C.R. Allen and H. Dalton, Org. Biomol. Chem., 2003, 1, 984-994.

Aerobic metabolism of 4-hydroxybenzoic acid in Archea via an unusual pathway involving an ‘NIH shift’, D.J. Fairley, M.J. Larkin, D.R. Boyd, N.D. Sharma and P. Morgan, Appl. Environ. Microbiol., 2002, 6246-6255.

Enzymatic and chemoenzymatic synthesis of arene trans-dihydrodiols, D.R. Boyd and N.D. Sharma, J. Mol. Cat. B: Enzymat., 2002, 19-20, 31-42.

Tandem enzyme-catalysed oxidations of alkyl phenyl sulfides and alkyl benzenes: Enantiocomplementary routes to chiral phenols, D.R. Boyd, N.D. Sharma, B.E. Byrne, S.D. Shepherd, V. Ljubez, C.C.R. Allen, L.A. Kulakov, M.L. Larkin and H. Dalton, Chem. Commun., 2002, 1914-1915.

Enzyme-catalysed oxygenation and deoxygenation routes to chiral thiosulfinates, D.R. Boyd, N.D. Sharma, M.A. Kennedy, S. Shepherd, J.F. Malone, A. Alves-Areias, R. Holt, S.G. Allenmark, M.A. Lemurell, H. Dalton and H. Luckarift, Chem. Commun., 2002, 1452-1453.

Novel oxidation products from guanine nucleosides reacted with dimethyldioxirane, R.J.H. Davies, C. Stevenson, S. Kumar, J. Lyle, L. Cosby, J.F. Malone, D.R. Boyd and N.D. Sharma, Chem. Commun., 2002, 1378-1379.

Dioxygenase-catalysed cis-dihydroxylation of pyridine ring systems, D.R. Boyd, N.D. Sharma, L.V. Modyanova, J.G. Carroll, J.F. Malone, C.C.R. Allen, J.T.G. Hamilton, D.T. Gibson, R.E. Parales and H. Dalton, Can. J. Chem, 2002, 80, 589-600.

Selectivity studies of the benzene cis-dihydrodiol dehydrogenase enzyme from Pseudomonas putida ML2 with vicinal diol substrates, C.C.R. Allen, D.R. Boyd, H. Dalton, N.A. Kerley, N.D. Sharma and C.E. Walker, Biocatalysis and biotransformations, 2002, 20, 257-264.

Aromatic dioxygenases: molecular biocatalysis and applications, D.R. Boyd, N.D. Sharma and C.C.R. Allen, Current Opinion in Biotechnology, 2001, 12, 564-573.