Abstract
A series of optically active stereoisomers of 3,4-methanoarginine (1-4 and ent-1-ent-4) with trans/cis, d/l, and syn/anti stereochemical diversity, the side-chains of which were restricted in various special arrangements, was designed as biologically useful arginine mimetics. These conformationally restricted arginine analogues were synthesized effectively by using a series of chiral 3,4-methanoamino acid equivalents (7-10 and ent-7-ent-10) as the key synthetic units. Their biological evaluation with three isoforms of nitric oxide synthase showed that trans-3,4-methano-l-syn-arginine (2) was a good substrate, having close potency to l-arginine, and isoforms selectivities were also similar to those of l-arginine.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 5984-5988 |
| Number of pages | 5 |
| Journal | Bioorganic and Medicinal Chemistry |
| Volume | 19 |
| Issue number | 20 |
| DOIs | |
| State | Published - Oct 15 2011 |
Keywords
- Arginine analogue
- Conformational restriction
- Cyclopropane
- Nitric oxide synthase
- Stereochemical diversity
ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry
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Cite this
Watanabe, M., Yamaguchi, K., Tang, W., Yoshida, K., Silverman, R. B., Arisawa, M., & Shuto, S. (2011). Synthesis of a series of 3,4-methanoarginines as side-chain conformationally restricted analogues of arginine. Bioorganic and Medicinal Chemistry, 19(20), 5984-5988. https://doi.org/10.1016/j.bmc.2011.08.049