We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Investigation of the Protection of the C4 Hydroxyl Group in Macrobicyclic Kdo Donors.
- Authors
Hamajima, Shogo; Komura, Naoko; Tanaka, Hide-Nori; Imamura, Akihiro; Ishida, Hideharu; Ichiyanagi, Tsuyoshi; Ando, Hiromune
- Abstract
Chemical synthesis of 3-deoxy-d-manno-2-octulosonic acid (Kdo)-containing glycans, such as bacterial lipopolysaccharides (LPSs) and capsular polysaccharides (CPSs), is in high demand for the development of vaccines against pathogenic bacteria. We have recently achieved the complete α-stereoselective glycosidation of Kdo using a macrobicyclic donor tethered at the C1 and C5 positions. In this study, to expand the scope of Kdo glycosidation, we sought to protect the 4-OH group, thereby shortening the reaction time and ensuring the conversion of the glycosyl acceptor via its selective removal. The protection of the 4-OH group influenced the reactivity of the Kdo donor, and the triisopropylsilyl (TIPS) group acted as a selectively removable booster. The 4-O-TIPS donor allowed the synthesis of the α(2,4)-linked dimeric Kdo sequence, which is widely found in bacterial LPSs.
- Subjects
HYDROXYL group; VACCINE development; PATHOGENIC bacteria; CHEMICAL synthesis; GLYCANS
- Publication
Molecules, 2023, Vol 28, Issue 1, p102
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28010102