Asymmetric synthesis of conformationally restricted L-arginine analogues as active site probes of nitric oxide synthase

RN Atkinson, L Moore, J Tobin…

Index: Atkinson; Moore; Tobin; King Journal of Organic Chemistry, 1999 , vol. 64, # 10 p. 3467 - 3475

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Citation Number: 29

Abstract

Using the catalytic asymmetric Sharpless carbamate aminohydroxylation, conformationally restricted l-arginine and l-homoarginine derivatives (5-8) were prepared in good enantiomeric excess to investigate the binding requirements of l-arginine-based compounds with nitric oxide synthase. The l-arginine derivatives (5 and 6) inhibited both the inducible and neuronal isoforms of nitric oxide synthase with little isoform selectivity (5, IC50= 42 ...