Synthesis of new polysialic acid derivatives.
In this paper we report the first synthesis of novel polysialic acid derivatives which is initiated by treatment of polysialic acid with EDC-HCl to yield the inter-residual delta-lactone. Subsequent reaction with amines or hydrazine gives the corresponding polysialic acid amides and hydrazide. Alkylation of the tetrabutylammonium salt of polysialic acid yields polysialic acid esters. In contrast a variety of N-derivatives of polysialic acid can be prepared starting from deacetylated polysialic acid. The N-derivatives prepared in this communication can be used for the Cu-catalyzed as well as Cu-free "click" chemistry.
Su
Yi
Y
Institut für Organische Chemie, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover, Germany.
Kasper
Cornelia
C
Kirschning
Andreas
A
Dräger
Gerald
G
Berski
Silke
S
D000215:Acylation; D000478:Alkylation; D000577:Amides; D057930:Click Chemistry; D004952:Esters; D006834:Hydrazines; D007783:Lactones; D012794:Sialic Acids / Q000138:chemical synthesis*
D000577:Amides; D004952:Esters; D006834:Hydrazines; D007783:Lactones; D012794:Sialic Acids; C021319:polysialic acid