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PMID: 20572672 Published · ppublish English Journal Article Research Support, N.I.H., Extramural

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

Organic letters ·Vol. 12 ·No. 14 ·2010-07-16 ·Pages 3269-71

Gaffney BL, Veliath E, Zhao J, Jones RA

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.

MeSH Terms

Cyclic GMP/analogs & derivatives,chemical synthesis,chemistry Kinetics Phosphates/chemical synthesis,chemistry Stereoisomerism

Chemicals

Phosphates bis(3',5')-cyclic diguanylic acid Cyclic GMP thiophosphoric acid

Authors & Affiliations

4 authors, click to expand affiliations / ORCID

Gaffney Barbara L

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

Veliath Elizabeth

Zhao Jianwei

Jones Roger A

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14 references, click to expand

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Article Info

Journal

Organic letters

Abbr.

Org Lett

ISSN

1523-7052

DOI

10.1021/ol101236b

Published

2010-07-16

Pages

3269-71

Language

English

Region

United States

NLM ID

100890393

PMCID

PMC2905038

Subset

Grants

NIGMS NIH HHS · R01 GM079760 · United States

NIGMS NIH HHS · R01 GM079760-08 · United States

NIGMS NIH HHS · GM79760 · United States

External Links

PubMed source DOI: 10.1021/ol101236b PMC Full Text View journal details

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

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