Premium
Stereocontrolled Synthesis of Lyso ‐phosphatidyl β‐D‐Glucoside
Author(s) -
Kano Koki,
Ishii Nozomi,
Hirabayashi Yoshio,
Kamiguchi Hiroyuki,
Greimel Peter,
Matsuo Ichiro
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202102176
Subject(s) - lyso , epimer , chemistry , axon guidance , protein subunit , stereochemistry , biochemistry , receptor , computer science , scintillator , telecommunications , detector , gene
Lyso ‐phosphatidyl β‐D‐glucoside (lysoPtdGlc) is during embryonic development a neurite growth cone guidance cue associated with G‐protein coupled receptor 55, and has been found to be involved in a variety of physiological and pathological events, including inflammatory pain, and cancer. Hence, the ability to prepare large quantities of lysoPtdGlc is an important objective. Herein, we report the convergent chemical synthesis of lysoPtdGlc and its glyceryl epimer ( S ‐lysoPtdGlc). High stereocontrol during β‐glycosyl H ‐phosphonate construction was achieved using a microfluidic approach, and common but undesirable regioisomerization due to acyl migration on the glyceryl subunit was successfully suppressed during deprotection. Purification of the final product was optimized to obtain sufficiently large amounts of lysoPtdGlc and S ‐lysoPtdGlc for biological assaying purposes.