Conversion of 7‐deoxy‐10‐deacetylbaccatin‐III into 6‐α‐hydroxy‐7‐deoxy‐10‐deacetylbaccatin‐III by<i>Nocardioides luteus</i>

Hanson, Ronald L.; Kant, Joydeep; Patel, Ramesh N.

doi:10.1042/ba20030093

Cited by 4 publications

(1 citation statement)

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“…We have previously reported the isolation of microbial strains containing C‐13 deacylase [3], C‐10 deacetylase [3] and C7‐xylosidase [4] enzyme activities, which are able to convert mixtures of taxanes into 10‐DAB (10‐deacetylbaccatin III), thereby increasing the amount and ease of isolation of this precursor for semisynthesis. We have also reported a strain able to hydroxylate 7‐deoxy‐10‐deacetylbaccatin‐III to 6‐hydroxy‐7‐deoxy‐10‐deacetylbaccatin‐III [5].…”

Section: Introductionmentioning

confidence: 99%

Enzymatic C‐4 deacetylation of 10‐deacetylbaccatin III

Hanson

Parker

Patel

2006

Biotech and App Biochem

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Second-generation paclitaxel analogues that require replacement of the C-4 acetate by other substituents are in development. An enzyme able to specifically remove the C-4 acetate from paclitaxel could simplify preparation of the analogues. Several strains were isolated from soil samples that contain enzyme activities able to 4-deacetylate 10-DAB (10-deacetylbaccatin III). Selection was made using plates containing 10-DAB as the sole carbon source and screening colonies for deacetylation of 10-DAB. Two strains initially isolated were identified as Rhodococcus sp. and deposited with the A.T.C.C. (Manassas, VA, U.S.A.) as strains 202191 and 202192. Whole cells were able to convert 10-DAB into 4,10-DDAB (4-deacetyl-10-deacetylbaccatin III) in 90% yield. The enzyme activity in these strains was not effective with paclitaxel and 10-deacetylpaclitaxel, although 4,10-DDAB was produced from baccatin III. The activity in these strains was associated with an insoluble fraction of cell extracts. Several additional isolates were obtained that were identified as variants of Stenotrophomonas maltophilia, and a soluble C-4 deacetylase was purified approx. 218-fold from one of them. The activity of this enzyme was limited to 10-DAB, and the enzyme was not effective with paclitaxel or baccatin III.

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Section: Introductionmentioning

confidence: 99%

Enzymatic C‐4 deacetylation of 10‐deacetylbaccatin III

Hanson

Parker

Patel

2006

Biotech and App Biochem

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Nocardioides

Evtushenko¹,

Krausova²,

Yoon³

2015

Bergey's Manual of Systematics of Archaea and Bacteria

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No.car.di.o.i'des. N.L. fem. n. Nocardia name of a genus; L. suff. ‐ oides (from Gr. suff. ‐ eides from Gr. n. eidos , that which is seen, form, shape, figure) ressembling, similar; N.L. masc. n. Nocardioides Nocardia ‐like, referring to the similarity of life cycles of the type species of this genus and Nocardia . Actinobacteria / Actinobacteria / Propionibacteriales / Nocardioidaceae / Nocardioides Abundantly branched vegetative hyphae or irregular rods may be formed in young cultures. The morphogenetic cycle is usually observable, with different organisms showing more or less complex succession of morphological stages . The morphogenetic cycle usually starts with the coccoid cells or short rods which may simply germinate into rods or longer filaments, show elementary branching or form extensively branched hyphae on and below the surface of agar media, and may give rise to aerial mycelium . The latter consists of irregular, sparsely branching or unbranched hyphae and may totally or partially cover the primary mycelium, or be discernible only microscopically. Both the vegetative and aerial hyphae and the rod‐shaped cells undergo various degrees of fragmentation (division via septa formation). Fragmentation finally results in the next generation of short rod‐like and coccoid cells. No endospores are formed. Rod‐shaped bacteria may be motile. Gram‐stain‐positive type of cell wall. Non‐acid‐fast. The colony color is mainly whitish, creamy, or yellow of different tint and intensity and rarely orange . Diffusible pigments are not usually produced. Colonies not covered by aerial mycelium are mostly pasty , with smooth to wrinkled surface . Chemo‐organotrophic, with an oxidative type of metabolism. Predominantly catalase‐positive. The level of oxidase activity varies among species. Grows under aerobic conditions on standard laboratory media, including chemically defined (synthetic) media or media with low nutrient concentrations. Certain vitamins or other growth factors may be required. Utilizes a wide range of carbon and nitrogen sources, including unusual organic compounds and toxic environmental pollutants. Mostly mesophilic and neutrophilic; some grow at initial pH values of 5–5.5 and/or 11–12. Mostly non‐halophilic, but salt‐requiring organisms occasionally occur. DNA G + C content ( mol %): 67.5 ( T m )–74.8 (HPLC). Type species : Nocardioides albus Prauser 1976, 61 AL .

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Phylum XXVI. Actinobacteria phyl. nov.

Goodfellow¹

2012

Bergey’s Manual® of Systematic Bacteriology

106

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Conversion of 7‐deoxy‐10‐deacetylbaccatin‐III into 6‐α‐hydroxy‐7‐deoxy‐10‐deacetylbaccatin‐III byNocardioides luteus

Cited by 4 publications

References 37 publications

Enzymatic C‐4 deacetylation of 10‐deacetylbaccatin III

Enzymatic C‐4 deacetylation of 10‐deacetylbaccatin III

Nocardioides

Phylum XXVI. Actinobacteria phyl. nov.

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