Mechanism and Stereochemistry of 5-Dehydroquinate Synthetase | Zendy

Samuel Rotenberg | Zendy; David B. Sprinson | Zendy

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Mechanism and Stereochemistry of 5-Dehydroquinate Synthetase

Author(s) -

Samuel Rotenberg,

David B. Sprinson

Publication year - 1970

Publication title -

proceedings of the national academy of sciences

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.011

H-Index - 771

eISSN - 1091-6490

pISSN - 0027-8424

DOI - 10.1073/pnas.67.4.1669

Subject(s) - tritium , dehydratase , chemistry , shikimic acid , stereochemistry , elimination reaction , enol , dehydration , biochemistry , enzyme , organic chemistry , catalysis , physics , nuclear physics

3-Deoxy-D-arabino -heptulosonic acid 7-phosphate (DAHP) labeled at C-7 randomly or stereospecifically with tritium and at C-1 with14 C was converted enzymically to 5-dehydroquinate. Tritium of all three substrates was completely retained in 5-dehydroquinate, in accord with formation of a non-ketonizing 6,7-enol intermediate. The 5-dehydroquinates were dehydrated to 5-dehydroshikimate by 5-dehydroquinate dehydratase, which is known to catalyze acis -elimination. Only 5-dehydroquinate derived from [7-3 H](7R )-DAHP lost its tritium in this dehydration, indicating that the configuration at C-7 was inverted in the conversion of DAHP to 5-dehydroquinate.

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