title: Synthesis and plant growth regulation activity of α-d-ManpNAc-(1→2)-[α-L-Rhap-(1→3)-]α-L-Rhap-(1→4)-β-d-GlupNAc-(1→3)-α-L-Rhap, the repeating unit of O-antigen of Rhizobium trifolii 4s.
abstract: The synthesis of a pentasaccharide 2 containing acetamido-2-deoxy-d-glucose and acetamido-2-deoxy-d-mannose related to the cell wall polysaccharide of Rhizobium trifolii 4s has been achieved by a [2+3] approach from commercially available l-rhamnose, d-glucose, and d-glucosamine as the starting materials. The target molecule was equipped with a p-methoxylphenyl handle at the reducing terminus to allow for further glycoconjugate formation via selective cleavage of this group. The bioassay suggested that the synthetic pentasaccharide 2 can stimulate the growth of wheat coleoptile similarly to indole-3-acetic acid (IAA), and promote the wheat seedling development before winter by seed treatment at a concentration of 20mg/L.
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors.forename: Guanghui
authors.initials: G
authors.lastname: Zong
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors.forename: Xiaomei
authors.initials: X
authors.lastname: Liang
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. Electronic address: zhangjianjun@cau.edu.cn.
authors.forename: Jianjun
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Engineering Research Centre of Plant Growth Regulators, Ministry of Education, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China.
authors.forename: Liusheng
authors.initials: L
authors.lastname: Duan
authors.affiliation: Engineering Research Centre of Plant Growth Regulators, Ministry of Education, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China. Electronic address: tanwm@cau.edu.cn.
authors.forename: Weiming
authors.initials: W
authors.lastname: Tan
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors.forename: Daoquan
authors.initials: D
authors.lastname: Wang
mesh_terms: D002240:Carbohydrate Sequence; D018548:Cotyledon / Q000187:drug effects / Q000254:growth & development; D005944:Glucosamine / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D008969:Molecular Sequence Data; D019081:O Antigens / Q000737:chemistry* / Q000494:pharmacology; D010937:Plant Growth Regulators / Q000138:chemical synthesis* / Q000494:pharmacology; D012210:Rhamnose / Q000737:chemistry; D012231:Rhizobium / Q000737:chemistry*; D036226:Seedlings / Q000187:drug effects / Q000254:growth & development; D014908:Triticum / Q000187:drug effects* / Q000254:growth & development
chemical_list: D019081:O Antigens; D010937:Plant Growth Regulators; D005947:Glucose; D005944:Glucosamine; D012210:Rhamnose
keywords: Oligosaccharide; Plant growth regulation activity; Rhizobium trifolii 4s; Synthesis