Substituent effects on the solution conformation of rifamycin S

Dampier, M. F.; Chen, C. W.

doi:10.1021/ja00438a055

Cited by 30 publications

(13 citation statements)

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“…6 ), 2 mM ascorbic acid was added to the Rif15 reactions to protect R-SV from oxidation (Fig. 2a , trace viii, ix) 26 . Upon this addition, we no longer detected R-L as a reaction product (Fig.…”

Section: Resultsmentioning

confidence: 99%

Deciphering the late steps of rifamycin biosynthesis

Zhang

et al. 2018

Nat Commun

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Rifamycin-derived drugs, including rifampin, rifabutin, rifapentine, and rifaximin, have long been used as first-line therapies for the treatment of tuberculosis and other deadly infections. However, the late steps leading to the biosynthesis of the industrially important rifamycin SV and B remain largely unknown. Here, we characterize a network of reactions underlying the biosynthesis of rifamycin SV, S, L, O, and B. The two-subunit transketolase Rif15 and the cytochrome P450 enzyme Rif16 are found to mediate, respectively, a unique C–O bond formation in rifamycin L and an atypical P450 ester-to-ether transformation from rifamycin L to B. Both reactions showcase interesting chemistries for these two widespread and well-studied enzyme families.

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Section: Resultsmentioning

confidence: 99%

Deciphering the late steps of rifamycin biosynthesis

Zhang

et al. 2018

Nat Commun

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“…The 1 H and 13 C NMR spectra of the rifamycins have been studied in detail by the groups of Gallo, 12b -d Whitlock 12e, 14 and Segre 4b in their investigations of the relationship between the solution conformation of this family of compounds and their biological activity. Exhaustive 1 H selective decoupling was employed to establish the assignment of the 13 C NMR spectrum of rifamycin S, 12d while its 1 H NMR assignment 4b,12c,e was based on selective irradiation experiments, D 2 O exchange and approximate chemical shift calculations.…”

Section: Resultsmentioning

confidence: 99%

NMR spectroscopic analysis of new spiro‐piperidylrifamycins

Rubio

Merino

García

et al. 2005

Magnetic Reson in Chemistry

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New spiro-piperidylrifamycin derivatives are presented. These compounds were synthesized from the reaction of 3-amino-4-iminorifamycin S and enantiomerically pure 4-piperidones, which generate diasteroisomeric rifabutin analogues with a new stereocentre at the spiranic carbon. The 1 H and 13 C NMR spectra of these new compounds, and also the configuration of the new stereogenic centres, were assigned using 2D NMR spectroscopic techniques. A preliminary study of the 1 H and 13 C NMR spectra of the starting compounds rifamycin S, 3-amino-4-iminorifamycin S and the related rifabutin was also carried out and as a result, their previously published 13 C NMR data were corrected.

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“…The 3-bromorifamycin SV was synthesized as described in [8] and hydrogenated over Rh/A1,0, leading, after oxidation with K,[Fe(CN),], to a mixture of the (16R)-and (16s)-epimers 7 and 8, respectively (Scheme 3), separable by CC. The hydroquinone form of 3 and 4, obtained by reduction of 3 and 4 with ascorbic acid [2], led by bromination [8] to 7 and 8, respectively.…”

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confidence: 99%

“…The hydroquinone form of 3 and 4, obtained by reduction of 3 and 4 with ascorbic acid [2], led by bromination [8] to 7 and 8, respectively.…”

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confidence: 99%