A Fluorescent Unnatural Mannosamine Derivative with Enhanced Emission Upon Complexation with Cucurbit[7]uril. Issue 1 (27th December 2022)

• Record Type: Journal Article
• Authors: Kataki‐Anastasakou, Anna; Jia, Shang; Axtell, Jonathan C.; Sletten, Ellen M.
• Other Names: Kramer Jessica R. guestEditor.; Pratt Matthew R. guestEditor.; Schumann Benjamin guestEditor.
• Is Part Of: Israel journal of chemistry. Volume 63:Issue 1/2(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-27
• Subjects: mannosamine -- fluorescence -- cucurbit[7]uril -- chemical reporter -- metabolic incorporation; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/ijch.202200069
• Languages: English
• ISSNs: 0021-2148

Abstract

Abstract: Metabolic incorporation of unnatural functionality on glycans has allowed chemical biologists to observe and affect cellular processes. Recent work has resulted in glycan‐fluorophore structures that allow for direct visualization of glycan‐mediated processes, shining light on their role in living systems. This work describes the serendipitous discovery of a small chemical reporter‐fluorophore. Investigations into the mechanism of fluorescence arising from (trimethylsilyl)methylglycine appended on mannosamine suggest rigidity and restriction of lone pair geometry contribute to the fluorescent behaviour. In fact, in situ cyclization and encapsulation in cucurbit[7]uril enhance fluorescence to levels that can be observed in live cells. While the reported unnatural mannosamine does not traverse the sialic acid biosynthetic pathway, this discovery may lead to small, "turn‐on" chemical reporters for incorporation in living systems. Abstract :