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Papers by Nicholas Camp

A variety of phosphonamidate-containing peptides were synthesised as potential inhibitors of the ... more A variety of phosphonamidate-containing peptides were synthesised as potential inhibitors of the HIV-1 protease. These transition state analogues were designed using known sequences from HIV-1 protease substrates and incorporated a unique Phe-Pro scissile bond mimic in an attempt to achieve selectivity over the mammalian aspartic proteases. Such compounds were found to be moderate inhibitors of the HiV-1 protease possessing iCgo values in the 1-100 pM range, both in in vitro and in vivo assays. However, the phosphonamidate methyl ester analogues showed a marked ability to enter ceils and this feature was highlighted in the 1:1 ratio of in vivo/ in vitro iCso values (generally for peptidic inhibitors, this ratio is 10-10000 fold higher, indicating poor cell uptake properties). Optimisation of the methyl ester analogues was attempted by alteration of the binding residues flanking either side of the phosphonamidate moiety. However, such alterations had only a small effect on inhibitor ...

Tetrahedron, Jan 7, 2000

A new and highly efficient synthesis of the potent nicotinic acetylcholine receptor agonist, anat... more A new and highly efficient synthesis of the potent nicotinic acetylcholine receptor agonist, anatoxin-a and its analogues is described, which uses a β-lactam ring opening–transannular cyclisation sequence to set up the bridged bicyclic framework of the natural product. The ...

Tetrahedron, 1996

A new mute to anatoxin-a (1) is reported which involves an anionically induced small ring opening... more A new mute to anatoxin-a (1) is reported which involves an anionically induced small ring opening / ring closure / ring opening cascade. The azabicyclo[4.2.1]nonane ring system of anatoxin-a is hence formed in one synthetic operation.

Journal of the Chemical Society, Chemical Communications, 1995

A new route to Anatoxin-a 1 is reported which involves a tandem methyllithium mediated ring openi... more A new route to Anatoxin-a 1 is reported which involves a tandem methyllithium mediated ring opening/intramolecular cyclisation as a key step to provide the required 2-acetyl-9-azabicyclo 14.2.1 I nonane ring structure in one synthetic operation.

Encyclopedic Reference of Immunotoxicology, 2005

Organic letters, Jan 3, 2014

The permanganate-mediated oxidative cyclization of a series of 2-methylenehept-5-eneoates bearing... more The permanganate-mediated oxidative cyclization of a series of 2-methylenehept-5-eneoates bearing different chiral auxiliaries was investigated, leading to the discovery of trans-2-tritylcyclohexanol (TTC) as a highly effective chiral controller for the formation of the 2,5-substituted THF diol product with high diastereoselectivity (dr ∼97:3). Chiral resolution of (±)-TTC, prepared in one step from cyclohexene oxide, afforded (-)-(1S,2R)-TTC (er >99:1), which was applied to the synthesis of (+)-trans-(2S,5S)-linalool oxide.

A variety of phosphonamidate-containing peptides were synthesised as potential inhibitors of the ... more A variety of phosphonamidate-containing peptides were synthesised as potential inhibitors of the HIV-1 protease. These transition state analogues were designed using known sequences from HIV-1 protease substrates and incorporated a unique Phe-Pro scissile bond mimic in an attempt to achieve selectivity over the mammalian aspartic proteases. Such compounds were found to be moderate inhibitors of the HiV-1 protease possessing iCgo values in the 1-100 pM range, both in in vitro and in vivo assays. However, the phosphonamidate methyl ester analogues showed a marked ability to enter ceils and this feature was highlighted in the 1:1 ratio of in vivo/ in vitro iCso values (generally for peptidic inhibitors, this ratio is 10-10000 fold higher, indicating poor cell uptake properties). Optimisation of the methyl ester analogues was attempted by alteration of the binding residues flanking either side of the phosphonamidate moiety. However, such alterations had only a small effect on inhibitor ...

Tetrahedron, Jan 7, 2000

A new and highly efficient synthesis of the potent nicotinic acetylcholine receptor agonist, anat... more A new and highly efficient synthesis of the potent nicotinic acetylcholine receptor agonist, anatoxin-a and its analogues is described, which uses a β-lactam ring opening–transannular cyclisation sequence to set up the bridged bicyclic framework of the natural product. The ...

Tetrahedron, 1996

A new mute to anatoxin-a (1) is reported which involves an anionically induced small ring opening... more A new mute to anatoxin-a (1) is reported which involves an anionically induced small ring opening / ring closure / ring opening cascade. The azabicyclo[4.2.1]nonane ring system of anatoxin-a is hence formed in one synthetic operation.

Journal of the Chemical Society, Chemical Communications, 1995

A new route to Anatoxin-a 1 is reported which involves a tandem methyllithium mediated ring openi... more A new route to Anatoxin-a 1 is reported which involves a tandem methyllithium mediated ring opening/intramolecular cyclisation as a key step to provide the required 2-acetyl-9-azabicyclo 14.2.1 I nonane ring structure in one synthetic operation.

Encyclopedic Reference of Immunotoxicology, 2005

Organic letters, Jan 3, 2014

The permanganate-mediated oxidative cyclization of a series of 2-methylenehept-5-eneoates bearing... more The permanganate-mediated oxidative cyclization of a series of 2-methylenehept-5-eneoates bearing different chiral auxiliaries was investigated, leading to the discovery of trans-2-tritylcyclohexanol (TTC) as a highly effective chiral controller for the formation of the 2,5-substituted THF diol product with high diastereoselectivity (dr ∼97:3). Chiral resolution of (±)-TTC, prepared in one step from cyclohexene oxide, afforded (-)-(1S,2R)-TTC (er >99:1), which was applied to the synthesis of (+)-trans-(2S,5S)-linalool oxide.

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