Catalytic antibodies in synthesis: Design and synthesis of a hapten for application to the preparation of a scalemic pyrrolidine ring synthon for ptilomycalin A
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作者:
Anderson, GT
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PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
Anderson, GT
[1
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Alexander, MD
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PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
Alexander, MD
[1
]
Taylor, SD
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PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
Taylor, SD
[1
]
Smithrud, DB
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PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
Smithrud, DB
[1
]
Benkovic, SJ
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PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
Benkovic, SJ
[1
]
Weinreb, SM
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PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
Weinreb, SM
[1
]
机构:
[1] PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
A catalytic antibody-based approach toward the synthesis of an optically active pyrrolidine ring synthon potentially useful for ptilomycalin A is described. Enantiomerically pure hapten 37 was designed and constructed with the eventual goal of generating antibodies for the enantioselective partial hydrolysis of a meso diester such as 44 into a monoacid 45. This transition state analog possesses a phosphonate group containing the requisite oxyanionic character of the tetrahedral intermediate for ester hydrolysis. A newly developed carbamate-based linker, which was found to be much more hydrolytically stable than the commonly used glutarate ester, was developed for coupling of the hapten to a carrier protein.