ORGN 555 |
A five-membered ring analog of 5-enolpyruvylshikimate-3-phosphate
| Ming An and Paul A. Bartlett. Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720 |
Shikimate and other intermediates of the shikimate-chorismate pathway are densely functionalized structures that seem to offer limited options for skeletal modification. We designed and synthesized cyclopentylidenes 1 and 2, as well as cyclopentenes 3 and 4, as novel ring-contracted analogs of shikimate. We previously reported that shikimate kinase (SK) converts analogs 1-3 to the five-membered ring analogs of shikimate-3-phosphate (S3P)--1P, 2P, and 3P. Here, we report that 5-Enolpyruvylshikimate-3-Phosphate (EPSP) synthase further processes cyclopentylidene-phosphate 2P to EP-2-P, a five-memebred ring analog of EPSP. These analogs show that ring-contraction of shikimate can be tolerated by SK and EPSP synthase. In the event, a two-step unnatural biosynthetic sequence is established for the shikimate-chorismate pathway.  |
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Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
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