28217-22-3Relevant articles and documents
Two-Enzyme Pathway Links l-Arginine to Nitric Oxide in N-Nitroso Biosynthesis
He, Hai-Yan,Henderson, Alyssa C.,Du, Yi-Ling,Ryan, Katherine S.
supporting information, p. 4026 - 4033 (2019/03/07)
Nitric oxide (NO) has wide-ranging roles in biology, but less is known about its role in building chemical diversity. Here we report a new route to NO from the biosynthetic pathway to the N-nitroso compound streptozocin. We show that the N-nitroso group of streptozocin comes from the biosynthetic reassembly of l-arginine, with the guanidino nitrogens forming a nitrogen-nitrogen bond. To understand this biosynthetic process, we identify the biosynthetic gene cluster of streptozocin and demonstrate that free l-arginine is N-methylated by StzE to give N?‰-monomethyl-l-arginine. We show that this product is then oxidized by StzF, a nonheme iron-dependent enzyme unrelated to known nitric oxide synthases, generating a urea compound and NO. Our work implies that formation and capture of NO is the likely route to N-nitroso formation in vivo. Altogether, our work unveils a new enzyme pair for the production of NO from l-arginine and sets the stage for understanding biosynthetic routes to N-nitroso natural products.
Thrombin inhibitors. I. Ester derivatives of N(α)-(arylsulfonyl)-L-arginine
Okamoto,Kinjo,Hijikata,et al.
, p. 827 - 830 (2007/10/02)
A series of N(α)(arylsulfonyl)-L-arginine esters was prepared and tested as inhibitors of the clotting activity of thrombin. N (α)Dansyl-L-arginine methyl ester was the most inhibitory of the N (α)(arylsulfonyl)-L-arginine methyl esters. The most potent inhibitors were the n-propyl and n-propyl esters of N(α)-dansyl-L-arginine with an I(50) of 2 x 10(-6) M. Esters of unsaturated straight-chain alcohols with a chain length of four carbons were also as inhibitory as the n-butyl ester. The inhibitors were hydrolyzed by thrombin and trypsin more slowly than N (α)-tosyl-L-arginine methyl ester.
