An Improved Stereoselective Synthesis of L‐Alanosine

Abstract

An improved, stereoselective synthesis of the natural, nonproteogenic amino acid L-alanosine has been developed, starting from the readily available and cheap substrate L-serine, in six steps and 49% overall yield. The process is very efficient, is suitable for large-scale production, and affords Lalanosine with properties comparable with those of the nat-

Biosynthesis of the N–N‐Bond‐Containing Compound l‐Alanosine

“…However, prior work shows that l-alanosine can be synthesized with a higher yield by using butyl nitrite as an organic nitrosylating reagent instead of NaNO 2 in acidic conditions. [34,35] However, we then tested the reaction of NOdonor diethylamine NONOate with l-N 3 -OH-Dap, and we Angewandte Chemie Communications observed significantly higher production of l-alanosine. With this reagent, the optimum pH is at around 6, with production even at pH 9 (Figure S7).…”

Biosynthesis of the N–N‐Bond‐Containing Compound l‐Alanosine

“…This reaction is likely to proceed via the nitrosonium ion, the production of which is thought to require acidic conditions. However, prior work shows that l ‐alanosine can be synthesized with a higher yield by using butyl nitrite as an organic nitrosylating reagent instead of NaNO 2 in acidic conditions . However, we then tested the reaction of NO‐donor diethylamine NONOate with l ‐ N 3 ‐OH‐Dap, and we observed significantly higher production of l ‐alanosine.…”

Foxo3a Inhibitors of Microbial Origin, JBIR-141 and JBIR-142

“…The UV data displayed a peak absorption band at 243 and 288 nm, which suggested the presence of an α-acyl tetramic acid moiety. The IR spectrum exhibited absorption bands for hydroxy (3350 cm –1 ), ester carbonyl (1733 and 1222 cm –1 ), amide carbonyl (1616 cm –1 ), and nitrosohydroxyamino (1457 cm –1 ) groups. − …”