The biosynthesis of mycophenolic acid

Canonica, L.; Kroszczynski, W.; Ranzi, B. M.; Rindone, B.; Scolastico, Carlo

doi:10.1039/c29700001357

Cited by 11 publications

(13 citation statements)

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“…The first insights into MPA biosynthesis, which were gained more than four decades ago from culture feeding studies using synthetic radioactive isotope labeling precursors, revealed its skeleton is derived from 5-methylorsellinic acid (5-MOA) and farnesyl pyrophosphate (FPP), and > a putative oxidative cleavage of the sesquiterpene (C 15 ) side chain (10–12). The C -methyl group at C6 and the O -methyl group at C5 were proposed to originate from S -adenosyl-L-methionine (SAM) (10, 13). However, the genetic and enzymological bases for MPA biosynthesis remained obscure until the recent independent discoveries of three analogous MPA biosynthetic gene clusters ( SI Appendix , Fig.…”

Section: Main Textmentioning

confidence: 99%

Compartmentalized Biosynthesis of Mycophenolic Acid

Zhang

et al. 2019

Preprint

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Section: Main Textmentioning

confidence: 99%

Compartmentalized Biosynthesis of Mycophenolic Acid

Zhang

et al. 2019

Preprint

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“…As biosynthetic evidence which indicates that C‐alkylation occurred preferentially in compounds having the m ‐dihydroxybenzene structure . Several attempts were made to introduce the side chain with the hydroxy ester 52 or with geraniol, or with trans , trans ‐ farnesol in the presence of p TsA or in an aqueous solution of acetic acid, or using ZnCl 2 and BF 3 etherate as catalyst on 63 failed.…”

Section: Reports Of the Total Synthesis Of Mycophenolic Acidmentioning

confidence: 99%

Mycophenolic Acid: Biogenesis, Compound Isolation, Biological Activity, and Historical Advances in Total Synthesis

et al. 2019

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The 6‐alkyl‐2,4‐dihydroxybenzoate moiety known commonly as resorcylate occurs widely as a building block in various fused cyclic systems of bioactive natural products and analogues. Among these many isolated active molecules, mycophenolic acid (MPA) was one of the most studied for its structural features and its potential biological activity. This perspective article portrays the unique biosynthetic interrelationships of polyketide formations in to resorcylates, which are implemented by recent biomimetic/chemical synthetic investigations of the natural product target. The resorcylate, MPA have remained as interesting targets for total synthesis in many laboratories worldwide. There are 13 syntheses reported for MPA to date (Scifinder search). The synthetic strategies for this potential lead compound was an evolution of various methods from generating the highly‐substituted aromatic system via employing simple and commercially available materials to the catalytic methods employed which always involve linear sequences; convergent approaches to the most important protecting group‐free syntheses are also briefly documented in this critical review. This natural product has been the subject of considerable synthetic study. Most reported total syntheses employ 6‐alkyl‐2,4‐hydroxybenzoic acids (lactones) as intermediates and proceed via stepwise derivatization to introduce other functionalities.

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“…Penicillic acid (49) M e w o ~O P. aurantiogriseum, P. vanbeymae, P. expansum, P. fennelliae, P. griseofulvum, P. madriti, P. puberulum, P. roquefortii, P. simplicissimum, P. thomii, P. viridicatum (P. M. Scott, 1977) (also Birkinshaw and GowHand, 1962;01ivigni and BuHerman, 1978;Mosbach, 1960) OH CH z Me Ac HOV Botryodiplodin (50) P. hirsutum (Fujimoto et at., 1980), P. roquefortii (Renauld et at., 1984) 6-Farnesyl-5, 7 -dihydroxy-4-methylphthalide (51) P. brevicompactum (Canonica et at., 1971) Mycochromenic acid (54) P. brevicompactum (Campbell et at., 1966;Bird and Campbell, 1982b;Colombo et aI., 1982) For mycophenolic acid, also: P. paxilli , P. roqueJortii (Lafont et at., 1979), P. otivicotor (Oxford and Raistrick, 1933) 3,7-Dimethyl-8-hydroxy-6-methoxy isochroman (61) P. citrinum (Cox et at., 1979) Canescin (62) P. canescens R) = H, R2 = H: Scott, 1977); P. viridicatum (P. M. Scott, 1977;Damoglou et al, 1984); P. purpurescens, P. roquefortii, P. spinulosum (Leistner and Pitt, 1977); P.janthinellum (Czech patent, 1982) Me P. viridicatum (Hutchison et al, 1971) 1 R = H: Ochratoxin A (72) P. viridicatum (van Walbeek et ai., 1969;van cler Merwe et al, 1965;Damoglou et al, 1984); P. aurantiogriseum, P. purpurescens, P. variabile, P.…”

Section: Coohmentioning

confidence: 99%

Penicillium and Acremonium

Peberdy¹

1987

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v Foreword Biotechnology is a word that was originally coined to describe the new processes which could be derived from our ability to manipulate, in vitro, the genetic material common to all organisms. I t has now become a generic term encompassing all "applications" of living systems, including the more traditional fermentation and agricultural industries. Recombinant DNA technology has opened up new opportunities for the exploitation of microorganisms and animal and plant cells as producers or modifiers of chemical and biological products.This series of handbooks deals exclusively with microorganisms which are at the forefront of the new technologies and brings together in each of its volumes the background information necessary to appreciate the historical development of the organisms making up a particular genus, the degree to which molecular biology has opened up new opportunities, and the place they occupy in today's biotechnology industry. Our aim was to make this primarily a practical approach, with emphasis on methodology, combining for the first time information which has largely been spread across a wide literature base or only touched upon briefly in review articles. Each handbook should provide the reader with a source text, from which the importance of the genus to his or her work can be identified, and a practical guide to the handling and exploitation of the organisms included.It is perhaps apt that Volume I of the series should deal with a group of organisms involved in producing chemicals which have dominated the fermentation and pharmaceutical industries for the past forty years-the antibiotics. In terms of the degree to which molecular biology has made an impact on this genus to date, it is clear that the major rewards are still to come.

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The biosynthesis of mycophenolic acid

Cited by 11 publications

References 0 publications

Compartmentalized Biosynthesis of Mycophenolic Acid

Compartmentalized Biosynthesis of Mycophenolic Acid

Mycophenolic Acid: Biogenesis, Compound Isolation, Biological Activity, and Historical Advances in Total Synthesis

Penicillium and Acremonium

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