1. Synthesis of a series of 3,4-methanoarginines as side-chain conformationally restricted analogues of arginine
- Author
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Watanabe, Mizuki, Yamaguchi, Kazuya, Tang, Wei, Yoshida, Keisuke, Silverman, Richard B., Arisawa, Mitsuhiro, and Shuto, Satoshi
- Subjects
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ARGININE , *ORGANIC synthesis , *CONFORMATIONAL analysis , *STEREOISOMERS , *NITRIC-oxide synthases , *STEREOCHEMISTRY , *CYCLOPROPANE - Abstract
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. [Copyright &y& Elsevier]
- Published
- 2011
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