Bacterial cleavage of nitrogen to sulfone bonds in sulfamide and 1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide: formation of 2-nitrobenzamide byGordoniasp.

Abstract

Pure cultures of aerobic bacteria were isolated which could utilize sulfamate, sulfamide or 1H‐2,1,3‐benzothiadiazin‐4(3H)‐one 2,2‐dioxide (BTDD) as sole source of sulfur for growth and thus cleave a N–S(O)x bond. The molar growth yields indicated that each source of sulfur was utilized quantitatively. This was confirmed directly for Gordonia sp. strain BT2 utilizing BTDD, which was converted quantitatively via an unidentified intermediate to 2‐nitrobenzamide. Another isolate, strain BT1, could utilize saccharin to yield salicylamide, thus cleaving both the N–S(O)x and C–S(O)x bonds.

Sulfamic Acid and Its N- and O-Substituted Derivatives

“…1171 Bacterial cleavage using four different cultures has been reported for the nitrogen−sulfur bond in sulfamide, sulfamate, cyclamate, saccharin, and 1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide. 1172 8.3.4. Seven-Membered Rings, Bicycles, and Multiring Heterocycles.…”