Synthetic studies on the lipooligosaccharide Nod Bj-IV (C18:1, Fuc, Gro) produced by Bradyrhizobium japonicum strain USDA61

Lipo-chitooligosaccharidic nodulation factors and their perception by plant receptors

“…The synthetic route also enabled the incorporation of four tritium atoms in the C16:2 fatty acid chain, providing a ligand identical to the genuine NodSm factor, with a specific radioactivity high enough to perform radioligand binding experiments [11]. Other groups further proposed alternative strategies for the synthesis of the NodSm factor [12][13][14] or the Nod factors produced by Bradyrhizobium japonicum, the symbiont of soybean [15]. The procedure established by Tailler et al [13] enabled the synthesis of a series of tetrameric sulfated LCOs differing for the structure of the fatty acid (length, degree and position of unsaturations) to perform structure-function studies [16].…”

Lipo-Chitooligosaccharidic Nodulation Factors: Synthesis and Agricultural Perspectives

“…It relies upon the N-phtalimido participating group at C(2) with glycosyl trichloroacetimidates 8 and a glycosyl fluoride to finally introduce the non-reducing unit (Box 3, Scheme 1). [11] These authors followed a similar sequence to access NodBj-V. [12] The strategy of Hui and colleagues represents a block synthesis with the preparation of the tetrasaccharide from two preformed disaccharidic moieties. [13] In this route, the non-reducing unit was introduced using a non-participating azido group at C(2), which differentiated this nitrogen from the others, introduced as participating Nphthalimido groups (Box 4, Scheme 1).…”