Patrick Perlmutter | Monash University (original) (raw)
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Papers by Patrick Perlmutter
Organic Letters, 2009
The first synthesis of carbon-stapled 3 -peptides is reported. The precursor 3 -peptides, with O-... more The first synthesis of carbon-stapled 3 -peptides is reported. The precursor 3 -peptides, with O-allyl -serines located in an i/i+3 relationship, were prepared on solid phase. We show that efficient ring-closing metathesis (RCM) of these new 3 -peptides proceeds smoothly either in solution or on an appropriate solid support. All products were generated with high selectivity for the E-isomer.
Journal of molecular recognition : JMR
In spite of the important role of angiotensin converting enzyme 2 (ACE2) in the cardiovascular sy... more In spite of the important role of angiotensin converting enzyme 2 (ACE2) in the cardiovascular system, little is known about the substrate structural requirements of the AngII-ACE2 interaction. Here we investigate how changes in angiotensin II (AngII) structure affect binding and cleavage by ACE2. A series of C3 β-amino acid AngII analogs were generated and their secondary structure, ACE2 inhibition, and proteolytic stability assessed by circular dichroism (CD), quenched fluorescence substrate (QFS) assay, and LC-MS analysis, respectively. The β-amino acid-substituted AngII analogs showed differences in secondary structure, ACE2 binding and proteolytic stability. In particular, three different subsets of structure-activity profiles were observed corresponding to substitutions in the N-terminus, the central region and the C-terminal region of AngII. The results show that β-substitution can dramatically alter the structure of AngII and changes in structure correlated with ACE2 inhibit...
Journal of the Chemical Society, Chemical Communications, 1990
ABSTRACT Phosphite esters can be used to give excellent regiocontrol in rhodium catalysed hydrofo... more ABSTRACT Phosphite esters can be used to give excellent regiocontrol in rhodium catalysed hydroformylation reactions of alkenes and in addition excellent stereocontrol in the reactions of some cyclohexenyl phosphites.
Journal of the Chemical Society, Chemical Communications, 1985
ABSTRACT Hydrocyanation of a range of protected β-hydroxyalkynes give unsaturated nitriles which ... more ABSTRACT Hydrocyanation of a range of protected β-hydroxyalkynes give unsaturated nitriles which can be cyclised to α-alkylidene γ-lactones and in most cases the regioselectivity of hydrocyanation can be controlled giving the desired cyanoalkenes with stereospecific formation of the E-isomer.
Tetrahedron Letters, 2009
We report an improved procedure for the selective transformation of substituted 1-tetralones to 1... more We report an improved procedure for the selective transformation of substituted 1-tetralones to 1,2-naphthoquinones by microwave-assisted selenium dioxide oxidation. The reaction time is effectively reduced from hours to seconds without any loss of yield (40–70%) or selectivity.
Proceedings of SPIE - The International Society for Optical Engineering
Here we report on using small unnatural helical beta peptides to form higher order geometries.. T... more Here we report on using small unnatural helical beta peptides to form higher order geometries.. These peptides are known to self-assemble by supramolecular recognition, via a unique 3-point H-bonding motif. This self-assembly pattern leads to unprecedented head-to-tail self-assembly, thus continuing the intramolecular helix into a fibrous superstructure. The smallest peptide still capable of self-assembly had a sequence of only three beta amino acids. We demonstrated a hierarchical self-assembly process, which can be designed to form macroscopic silk-like threads as well as complex nanometer scale surface structures. We have achieved radial as well as parallel geometries. Both the synthesis and the derivatization of the fibres is relatively straigthforward, making this platform technology ideally suited for the highly exacting requirements of materials science.
Current pharmaceutical design
With recent advances in the design and delivery of peptide-based therapeutics there has been a gr... more With recent advances in the design and delivery of peptide-based therapeutics there has been a growing interest on the use of peptides in vaccine design. Moreover, functional dissection and proteomic analysis of the immunogenic epitopes of proteins from pathogenic micro-organisms, cancers and self-tissues targeted by autoimmune responses, have broadened the range of target epitopes and given clues to enhancing peptide immunogenicity. Consistent with these observations; peptides can be synthesised with defined chemical modifications to mimic natural epitopes and/or deliberately introduce protease resistant peptide bonds to regulate their processing independent of tissue specific proteolysis and to stabilize these compounds in vivo. We discuss the potential of peptide-based vaccines for the treatment of chronic viral diseases and cancer and review recent developments in the field of epitope discovery and peptide-based vaccines.
ChemInform, 1996
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Australian Journal of Chemistry
A new, one-pot annulation process, involving conjugate addition of the sodium salts of dimethyl (... more A new, one-pot annulation process, involving conjugate addition of the sodium salts of dimethyl (or dibenzyl ) malonate to alkyl 2-(1- hydroxyalkyl ) propenoates, produces a mixture of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates. Alkylations of the cis-isomers were found to be highly stereoselective . The ntroduction of unsaturation into these molecules is also described.
Acta Crystallographica Section C Crystal Structure Communications
Australian Journal of Chemistry
A direct method for the preparation of C 5-alkoxycarbonyl-substituted 2,8-dioxabicyclo[3.2.1]octa... more A direct method for the preparation of C 5-alkoxycarbonyl-substituted 2,8-dioxabicyclo[3.2.1]octanes is described. The key process involves a highly stereoselective (NARC) sequence of a nucleophilic addition followed by ring closure.
ChemInform
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Organic Letters, 2009
The first synthesis of carbon-stapled 3 -peptides is reported. The precursor 3 -peptides, with O-... more The first synthesis of carbon-stapled 3 -peptides is reported. The precursor 3 -peptides, with O-allyl -serines located in an i/i+3 relationship, were prepared on solid phase. We show that efficient ring-closing metathesis (RCM) of these new 3 -peptides proceeds smoothly either in solution or on an appropriate solid support. All products were generated with high selectivity for the E-isomer.
Journal of molecular recognition : JMR
In spite of the important role of angiotensin converting enzyme 2 (ACE2) in the cardiovascular sy... more In spite of the important role of angiotensin converting enzyme 2 (ACE2) in the cardiovascular system, little is known about the substrate structural requirements of the AngII-ACE2 interaction. Here we investigate how changes in angiotensin II (AngII) structure affect binding and cleavage by ACE2. A series of C3 β-amino acid AngII analogs were generated and their secondary structure, ACE2 inhibition, and proteolytic stability assessed by circular dichroism (CD), quenched fluorescence substrate (QFS) assay, and LC-MS analysis, respectively. The β-amino acid-substituted AngII analogs showed differences in secondary structure, ACE2 binding and proteolytic stability. In particular, three different subsets of structure-activity profiles were observed corresponding to substitutions in the N-terminus, the central region and the C-terminal region of AngII. The results show that β-substitution can dramatically alter the structure of AngII and changes in structure correlated with ACE2 inhibit...
Journal of the Chemical Society, Chemical Communications, 1990
ABSTRACT Phosphite esters can be used to give excellent regiocontrol in rhodium catalysed hydrofo... more ABSTRACT Phosphite esters can be used to give excellent regiocontrol in rhodium catalysed hydroformylation reactions of alkenes and in addition excellent stereocontrol in the reactions of some cyclohexenyl phosphites.
Journal of the Chemical Society, Chemical Communications, 1985
ABSTRACT Hydrocyanation of a range of protected β-hydroxyalkynes give unsaturated nitriles which ... more ABSTRACT Hydrocyanation of a range of protected β-hydroxyalkynes give unsaturated nitriles which can be cyclised to α-alkylidene γ-lactones and in most cases the regioselectivity of hydrocyanation can be controlled giving the desired cyanoalkenes with stereospecific formation of the E-isomer.
Tetrahedron Letters, 2009
We report an improved procedure for the selective transformation of substituted 1-tetralones to 1... more We report an improved procedure for the selective transformation of substituted 1-tetralones to 1,2-naphthoquinones by microwave-assisted selenium dioxide oxidation. The reaction time is effectively reduced from hours to seconds without any loss of yield (40–70%) or selectivity.
Proceedings of SPIE - The International Society for Optical Engineering
Here we report on using small unnatural helical beta peptides to form higher order geometries.. T... more Here we report on using small unnatural helical beta peptides to form higher order geometries.. These peptides are known to self-assemble by supramolecular recognition, via a unique 3-point H-bonding motif. This self-assembly pattern leads to unprecedented head-to-tail self-assembly, thus continuing the intramolecular helix into a fibrous superstructure. The smallest peptide still capable of self-assembly had a sequence of only three beta amino acids. We demonstrated a hierarchical self-assembly process, which can be designed to form macroscopic silk-like threads as well as complex nanometer scale surface structures. We have achieved radial as well as parallel geometries. Both the synthesis and the derivatization of the fibres is relatively straigthforward, making this platform technology ideally suited for the highly exacting requirements of materials science.
Current pharmaceutical design
With recent advances in the design and delivery of peptide-based therapeutics there has been a gr... more With recent advances in the design and delivery of peptide-based therapeutics there has been a growing interest on the use of peptides in vaccine design. Moreover, functional dissection and proteomic analysis of the immunogenic epitopes of proteins from pathogenic micro-organisms, cancers and self-tissues targeted by autoimmune responses, have broadened the range of target epitopes and given clues to enhancing peptide immunogenicity. Consistent with these observations; peptides can be synthesised with defined chemical modifications to mimic natural epitopes and/or deliberately introduce protease resistant peptide bonds to regulate their processing independent of tissue specific proteolysis and to stabilize these compounds in vivo. We discuss the potential of peptide-based vaccines for the treatment of chronic viral diseases and cancer and review recent developments in the field of epitope discovery and peptide-based vaccines.
ChemInform, 1996
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Australian Journal of Chemistry
A new, one-pot annulation process, involving conjugate addition of the sodium salts of dimethyl (... more A new, one-pot annulation process, involving conjugate addition of the sodium salts of dimethyl (or dibenzyl ) malonate to alkyl 2-(1- hydroxyalkyl ) propenoates, produces a mixture of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates. Alkylations of the cis-isomers were found to be highly stereoselective . The ntroduction of unsaturation into these molecules is also described.
Acta Crystallographica Section C Crystal Structure Communications
Australian Journal of Chemistry
A direct method for the preparation of C 5-alkoxycarbonyl-substituted 2,8-dioxabicyclo[3.2.1]octa... more A direct method for the preparation of C 5-alkoxycarbonyl-substituted 2,8-dioxabicyclo[3.2.1]octanes is described. The key process involves a highly stereoselective (NARC) sequence of a nucleophilic addition followed by ring closure.
ChemInform
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.