Highly reactive "RIKEN click" probe for glycoconjugation on lysines. Issue 20 (17th May 2017)

• Record Type: Journal Article
• Authors: Sibgatullina, Regina; Fujiki, Katsumasa; Murase, Takefumi; Yamamoto, Takahiro; Shimoda, Taiji; Kurbangalieva, Almira; Tanaka, Katsunori
• Is Part Of: Tetrahedron letters. Volume 58:Issue 20(2017)
• Page Start: 1929
• Page End: 1933
• Publication Date: 2017-05-17
• Subjects: RIKEN click reaction -- N-Glycoalbumin -- Asparagine-linked glycans (N-glycans) -- Glycoconjugation -- Lysine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.03.081
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A highly amine-reactive "RIKEN click" probe was developed. The probe was synthesized from commercially available materials with good yields. "RIKEN click" reaction becomes one of the best techniques for glycan conjugation. Abstract: One pot double click strategy containing strain-promoted click-reaction followed by 6π-azaelectrocyclization (RIKEN click reaction) has worked well in the synthesis of multivalent homogeneous and heterogeneous N -glycoalbumins. We have slightly changed the structure of linker unsaturated aldehyde used in this method. As a result it can be easily synthesized from commercially available material and furthermore, the enhancement of its reactivity towards both click-reactions was observed. The data described in this Communications facilitate the usage of the double click strategy as a general method for the synthesis of a variety of neo- N -glycoproteins.