One-flask syntheses of c-di-GMP and the [ R p, R p] and [ R p, S p] thiophosphate analogues

Barbara L. Gaffney; Elizabeth Veliath; Jianwei Zhao; Roger A. Jones

doi:10.1021/ol101236b

One-flask syntheses of c-di-GMP and the [ R _p, R _p] and [ R _p, S _p] thiophosphate analogues

Barbara L. Gaffney, Elizabeth Veliath, Jianwei Zhao, Roger A. Jones

School of Arts and Sciences, Chemistry & Chemical Biology

Research output: Contribution to journal › Article › peer-review

97 Scopus citations

Abstract

(Figure Presented) 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.

Original language	English (US)
Pages (from-to)	3269-3271
Number of pages	3
Journal	Organic letters
Volume	12
Issue number	14
DOIs	https://doi.org/10.1021/ol101236b
State	Published - Jul 16 2010

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol101236b

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abstract = "(Figure Presented) 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 [Rp,Rp] and [Rp,Sp] 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.",

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T1 - One-flask syntheses of c-di-GMP and the [ R p, R p] and [ R p, S p] thiophosphate analogues

AU - Gaffney, Barbara L.

AU - Veliath, Elizabeth

AU - Zhao, Jianwei

AU - Jones, Roger A.

PY - 2010/7/16

Y1 - 2010/7/16

N2 - (Figure Presented) 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 [Rp,Rp] and [Rp,Sp] 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.

AB - (Figure Presented) 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 [Rp,Rp] and [Rp,Sp] 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.

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One-flask syntheses of c-di-GMP and the [ R _p, R _p] and [ R _p, S _p] thiophosphate analogues

Abstract

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