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Org Lett. 2010 Jul 16;12(14):3269-71. doi: 10.1021/ol101236b.

One-flask syntheses of c-di-GMP and the [Rp,Rp] and [Rp,Sp] thiophosphate analogues.

Author information

1
Department of Chemistry and Chemical Biology, 610 Taylor Road, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.

Abstract

An integrated set of reactions and conditions that allow an eight-step one-flask synthesis of the protected derivatives of c-di-GMP and the [R(p),R(p)] and [R(p),S(p)] thiophosphate analogues is reported. Deprotection is also carried out as a one-flask procedure, with the final products isolated by crystallization from the reaction mixture. Chromatography is only used for separation of the thiophosphate diastereomers.

PMID:
20572672
PMCID:
PMC2905038
DOI:
10.1021/ol101236b
[Indexed for MEDLINE]
Free PMC Article

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