title: Synthesis of a new glycosphingolipid, neurosporaside, from Neurospora crassa.
abstract: The glycosphingolipid neurosporaside (α-D-Glcp-(1 → 2)-β-D-Galp-(1 → 6)-β-D-Galp-(1 → 6)-β-D-Galp-(1 →)-Cer) occurs in Neurospora crassa. We attempted to synthesize neurosporaside by block synthesis (route A) and linear synthesis (route B). Oligosaccharide derivatives were synthesized using trimethylsilyltrifluoromethanesulfonate and N-iodosuccinimide/trifluoromethane sulfonic acid as promoters. The target tetrasaccharide could not be attained via route A, but route B showed potential: glycosidic bonds (β-D-Galp-(1 → 6)-β-D-Galp-(1 → 6)-β-D-Galp) were formed stereoselectively, leading to the synthesis of glycosphingolipid 2.
authors: School of Pharmaceutical Sciences, Kyushu University of Health and Welfare, 1714-1 Yoshino-cho, Nobeoka City, Miyazaki 882-8508, Japan. Electronic address: ohtsuka@phoenix.ac.jp.
authors: Isao
authors: I
authors: Ohtsuka
authors: Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan.
authors: Noriyasu
authors: N
authors: Hada
authors: School of Pharmaceutical Sciences, Kyushu University of Health and Welfare, 1714-1 Yoshino-cho, Nobeoka City, Miyazaki 882-8508, Japan.
authors: Misaki
authors: M
authors: Kanemaru
authors: School of Pharmaceutical Sciences, Kyushu University of Health and Welfare, 1714-1 Yoshino-cho, Nobeoka City, Miyazaki 882-8508, Japan.
authors: Takanari
authors: T
authors: Fujii
authors: School of Pharmaceutical Sciences, Kyushu University of Health and Welfare, 1714-1 Yoshino-cho, Nobeoka City, Miyazaki 882-8508, Japan.
authors: Toshiyuki
authors: T
authors: Atsumi
authors: School of Pharmaceutical Sciences, Kyushu University of Health and Welfare, 1714-1 Yoshino-cho, Nobeoka City, Miyazaki 882-8508, Japan.
authors: Nobuko
authors: N
authors: Kakiuchi
mesh_terms: D002236:Carbohydrate Conformation; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry; D009492:Neurospora crassa / Q000737:chemistry*; D013237:Stereoisomerism; D013388:Succinimides / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry
chemical_list: D006028:Glycosphingolipids; D008698:Mesylates; D013388:Succinimides; D014297:Trimethylsilyl Compounds; C558964:neurosporaside; C053353:trimethylsilyl trifluoromethanesulfonate; C008155:N-iodosuccinimide; C012077:trifluoromethanesulfonic acid
keywords: Glycosphingolipid; Neurospora crassa; Neurosporaside; Oligosaccharide synthesis