(Hemi)synthesis of ribazole-2′,3′-cyclophosphate: a key building block in cobamide chemistry
Abstract
This study presents a quick and effective method for producing α-ribazole-2',3'-cyclophosphate from vitamin B 12 . Using an optimized microwave-assisted cyanolysis, α-ribazole-2',3'-cyclophosphate was obtained in a high isolated yield of 90% after purification by silica column chromatography. This method was compared to a revised total synthesis route where α-ribazole was produced in six steps with a 34% overall yield. This was followed by an optimized microwave-assisted cyclophosphorylation step that afforded α-ribazole-2',3'-cyclophosphate in 42% yield. Both synthetic strategies were monitored by UHPLC-MS and UHPLC-fluorescence to ensure the confirmation and quantification conversions as well as to optimize the synthesis conditions. Finally, spectroscopic studies and pH-dependent analyses have shown that the protonation of the benzimidazole moiety ( pK a values) is virtually unaffected by structural variations. Furthermore, the emission properties of α-ribazole and its cyclophosphate analogue have been found to be comparable, which confirms the validity of the analytical approaches used to monitor and quantify them.
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BibTeX
@article{borg2026hemisynthesis,
title = {{(Hemi)synthesis of ribazole-2′,3′-cyclophosphate: a key building block in cobamide chemistry}},
author = {Antoine Borg and Louis Evrard and Corentin Maire and Loan Regaudie and Garoa Magunazelaia Usobiaga and Valérie Mazan and Arthur de Clerck and Stéphane Le Calvé and Mourad Elhabiri},
journal = {Organic \& Biomolecular Chemistry},
year = {2026},
month = oct,
doi = {10.1039/d6ob00916f},
url = {https://hal.science/hal-05839063v1},
note = {CC BY-NC 4.0},
}
RIS
TY - JOUR
TI - (Hemi)synthesis of ribazole-2′,3′-cyclophosphate: a key building block in cobamide chemistry
AU - Antoine Borg
AU - Louis Evrard
AU - Corentin Maire
AU - Loan Regaudie
AU - Garoa Magunazelaia Usobiaga
AU - Valérie Mazan
AU - Arthur de Clerck
AU - Stéphane Le Calvé
AU - Mourad Elhabiri
PY - 2026
DA - 2026/10/26
JO - Organic & Biomolecular Chemistry
DO - 10.1039/d6ob00916f
UR - https://hal.science/hal-05839063v1
AB - This study presents a quick and effective method for producing α-ribazole-2',3'-cyclophosphate from vitamin B 12 . Using an optimized microwave-assisted cyanolysis, α-ribazole-2',3'-cyclophosphate was obtained in a high isolated yield of 90% after purification by silica column chromatography. This method was compared to a revised total synthesis route where α-ribazole was produced in six steps with a 34% overall yield. This was followed by an optimized microwave-assisted cyclophosphorylation step that afforded α-ribazole-2',3'-cyclophosphate in 42% yield. Both synthetic strategies were monitored by UHPLC-MS and UHPLC-fluorescence to ensure the confirmation and quantification conversions as well as to optimize the synthesis conditions. Finally, spectroscopic studies and pH-dependent analyses have shown that the protonation of the benzimidazole moiety ( pK a values) is virtually unaffected by structural variations. Furthermore, the emission properties of α-ribazole and its cyclophosphate analogue have been found to be comparable, which confirms the validity of the analytical approaches used to monitor and quantify them.
SN - 1477-0520
SN - 1477-0539
ER -