The chemistry of pseudomonic acid. Part 1. The absolute configuration of pseudomonic acid A

Alexander, Roger G.; Clayton, J. P.; Luk, Kong; Rogers, Norman H.; King, Trevor J.

doi:10.1039/p19780000561

Cited by 40 publications

(11 citation statements)

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“…The polyketide mupirocin (1) is produced by Pseudomonas fluorescens as a mixture of pseudomonic acids (A-D). [23][24][25][26][27] Its structure is a monic acid (C 17 -ketide) with a pyran ring linked by an ester to 9-hydroxynonanoic acid (9-HN) 26,27 (Fig. 3).…”

Section: Mmpc Involved In Mupirocin Biosynthesismentioning

confidence: 99%

Discrete acyltransferases involved in polyketide biosynthesis

Musiol

Weber

2012

Med. Chem. Commun.

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Section: Mmpc Involved In Mupirocin Biosynthesismentioning

confidence: 99%

Discrete acyltransferases involved in polyketide biosynthesis

Musiol

Weber

2012

Med. Chem. Commun.

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“…where J((o,), the spectral density function, is givens5 by [3] ... [3] and 2z J( wf)= l+ (Oj'° z° F0=-7h•3°•h r 1c14 [4] ... where rcH is the carbon, hydrogen bond length (1.1 A here8) and;,,,, w" and Ic, we are the magnetogyric ratios and Larmor frequencies (radians/second) for hydrogen and carbon respectively. The effective correlation time (z) is the weighted average of all the separate correlation times that contribute to the overall motion of a particular carbon.')…”

Section: Discussionmentioning

confidence: 99%

Segmental motion in pseudomonic acid A: A carbon-13 spin-lattice relaxation time study at two field strengths.

Everett

Tyler

1984

J. Antibiot.

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The mobility of pseudomonic acid A in dimethyl sulfoxide-d3 solution has been determined from 13C spin-lattice relaxation time measurements at two field strengths. The central tetrahydropyran ring reorientates isotropically with a rotational correlation time of -280 picoseconds/radian.Both side-chains exhibit marked segmental motion with correlation times decreasing to only -50 picoseconds/radian at the end of the nonanoic acid side-chain.Pseudomonic acid A is a naturally occurring antibiotic produced by fermentation of a strain of Pseudomonas flourescens.l" The gross structure was elucidated on the basis of spectroscopic and degradative data.'' This structure was confirmed and the absolute stereochemistry shown to be I by further spectroscopic and X-ray work.3)We have now measured the 13C spin-lattice relaxation times (T1's) of all the carbon atoms in I in order to gain information about the mobility of I in solution. This information is potentially useful in the understanding of both the biological activity of I and also the interaction of I with other molecules and ions in solution. The T1 data has also served as a check on the 13C spectral assignments.Results Table 1 gives the 20 MHz 13C T1 and nuclear overhauser effect (NOE) results, the 63 MHz 13C T1and NOE results and the effective 13C correlation times for a dimethyl sulfoxide-de solution of I. Fig. 1 shows three partially relaxed 63 MHz 13C spectra of I in dimethyl sulfoxide-de. ExperimentalAll experiments were conducted at ambient temperature on -0.6 M solutions of pseudomonic acid A in DMSO-de. The 20 MHz 13C NMR data was acquired on a Bruker WP 80 using 10 mm tubes. The sweep width was 3787.9 Hz over 8 K data points.The 90° pulse for 13C was -17 pseconds. The free induction decays (FIDs) were zero-filled to 16 K points and a line broadening of 1 to 1.5 Hz was applied prior to Fourier transformation.The 63 MHz 13C data was acquired on a Bruker WM250 using 5 mm tubes in a 13C/1H dual probe.The sweep width was 11627.9 Hz over 16 K data points. The 90° pulse for 13C was -10 lrseconds.

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“…They are potent inhibitors of Gram-positive pathogens. 191, 192 Mupirocin W and H belong to another class of antibiotics isolated from Pseudomonas fluorescens which display similar bioactivity to pseudomonic acids. 193, 194 Thiomarinols were recently isolated from marine bacterium Pseudoalteromonas sp.…”

Section: Introductionmentioning

confidence: 99%

Achmatowicz reaction and its application in the syntheses of bioactive molecules

Ghosh

Brindisi

2016

RSC Adv.

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Substituted pyranones and tetrahydropyrans are structural subunits of many bioactive natural products. Considerable efforts are devoted toward the chemical synthesis of these natural products due to their therapeutic potential as well as low natural abundance. These embedded pyranones and tetrahydropyran structural motifs have been the subject of synthetic interest over the years. While there are methods available for the syntheses of these subunits, there are issues related to regio and stereochemical outcomes, as well as versatility and compatibility of reaction conditions and functional group tolerance. The Achmatowicz reaction, an oxidative ring enlargement of furyl alcohol, was developed in the 1970s. The reaction provides a unique entry to a variety of pyranone derivatives from functionalized furanyl alcohols. These pyranones provide convenient access to substituted tetrahydropyran derivatives. This review outlines general approaches to the synthesis of tetrahydropyrans, covering general mechanistic aspects of the Achmatowicz reaction or rearrangement with an overview of the reagents utilized for the Achmatowicz reaction. The review then focuses on the synthesis of functionalized tetrahydropyrans and pyranones and their applications in the synthesis of natural products and medicinal agents.

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The chemistry of pseudomonic acid. Part 1. The absolute configuration of pseudomonic acid A

Cited by 40 publications

References 0 publications

Discrete acyltransferases involved in polyketide biosynthesis

Discrete acyltransferases involved in polyketide biosynthesis

Segmental motion in pseudomonic acid A: A carbon-13 spin-lattice relaxation time study at two field strengths.

Achmatowicz reaction and its application in the syntheses of bioactive molecules

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