Enzymatic synthesis of l -6-hydroxynorleucine

Hanson, Ronald L.; Schwinden, Mark D.; Banerjee, Amit; Brzozowski, David B.; Chen, Bang‐Chi; Patel, Bhiku; McNamee, Clyde G.; Kodersha, Gus A.; Kronenthal, David R.; Patel, Ramesh N.; Szarka, Laszlo J.

doi:10.1016/s0968-0896(99)00158-3

Cited by 87 publications

(42 citation statements)

References 17 publications

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“…For solubility, the substituted boronic acids (1-5) and diol 12 were measured in a 2:1 (v/v) mixture of water and methanol; the remaining diols and hydroxy acids were measured in water. Following acidity constant determination, a mixture of a boronate (1-5) and a diol (9)(10)(11)(12) or hydroxy acid (13)(14)(15)(16)(17)(18)(19) was titrated to produce a titration curve that was analyzed by points per equivalent. The statistical fits in all cases exceeded the expectations at the 95% confidence interval.…”

Section: Resultsmentioning

confidence: 99%

Phenyl boronic acid complexes of diols and hydroxyacids

Bromba

Carrie

Chui

et al. 2009

Supramolecular Chemistry

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Abstract:Cumulative formation constants for the interaction of phenylboronic acids with 1,2-diols and structurally related α-hydroxy carboxylic acids were determined by potentiometric titration in aqueous solution. Although there is a significant electronic effect on the acidity of phenylboronic acid (ρ = 2.1), there is no marked electronic effect on the stability of the complexes. Rather, the complexes are significantly destabilized by adjacent anionic groups, by steric interactions across the face of the cyclic boronate ester, and by angle strain within the boronate ester ring. Binding that is nearly independent of pH is observed for some favorably constituted α-hydroxy acid complexes as a result of the relatively high acidity of the acids, which in turn allows tetrahedral boronate complexes to persist in acidic solution (pH < 3).

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Section: Resultsmentioning

confidence: 99%

Phenyl boronic acid complexes of diols and hydroxyacids

Bromba

Carrie

Chui

et al. 2009

Supramolecular Chemistry

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“…Accumulation of glucono-1,5-lactone in GDH regenerated processes over a time period of 2 h. Solid lines, NADH regeneration; dashed lines, NADPH regeneration. Data for modeling (glucose conversion rates, coenzyme concentration, pH) are taken from the indicated references: a, synthesis of l-6-hydroxynorleucine; [13] b, synthesis of actinol; [9] c, synthesis of l-leucovorin; [16] d, synthesis of methyl (R)-o-chloromandelate; [4] e, synthesis of l-carnitine; [12] f, synthesis of l-glyceraldehyde; [11] g, synthesis of (R)-ethyl 2-methyl 4-oxo-2-pentanoate; [10] h, synthesis of (R)-1-phenyl-A C H T U N G T R E N N U N G ethanol. [14] The pH-dependent glucono-1,5-lactone hydrolysis rates were taken from.…”

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confidence: 99%

Guidelines for the Application of NAD(P)H Regenerating Glucose Dehydrogenase in Synthetic Processes

et al. 2013

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Glucose dehydrogenase (GDH) is frequently used for the reduction of NAD + and NADP + in bench-and industrial-scale syntheses because the coenzyme regenerating system GDH is easy to apply, robust and relatively inexpensive. To optimize the application of this long known coenzyme regeneration system we investigated the commonly applied Bacillus GDH and characterized this enzyme by its kinetic features in the presence of substrates and products at pH 6.4 and 8.0. Three substrates/products were found to inhibit GDH considerably: (i) the reaction product glucono-1,5-lactone, (ii) the reduced coenzyme NAD(P)H and (iii) the oxidized coenzyme NAD(P)+ . The inhibition of GDH under several process conditions was modeled using the determined kinetic constants. It was found that the GDH regeneration system is strongly inhibited by the usually applied conditions. This study provides the rate equation of the GDH reaction and simulations of this coenzyme regenerating system leading to an improved prediction and, thus, to a faster scale-up and increased efficiency of NAD(P)H-dependent synthetic processes.

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“…Thus the preparation of paclitaxel by semi--synthetic process eliminates cutting down the large yew trees. By using selective enrichment techniques, two strains of Nocardioides were isolated from soil samples that contained novel enzymes C-13 taxolase, C-10 deacetylase and C-7 xylosidase (44)(45)(46). The extracellular C-13 taxolase derived from the filtrate of the fermentation broth of Nocardioides albus SC 13911 [Scheme 8A] catalyzed the cleavage of C-13 side-chain from paclitaxel and related taxanes such as taxol C, cephalomannine, 7-b-xylosyltaxol, 7-b-xylosyl-10-deacetyltaxol, and 10-deacetyltaxol [Scheme 8A].…”

Section: Microbial Hydroxylation Of Pleuromutilin or Mutilinmentioning

confidence: 99%

Biocatalytic Synthesis of Chiral Pharmaceutical Intermediates

Patel

2005

ChemInform

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SummaryThe production of single enantiomers of drug intermediates has become increasingly important in the pharmaceutical industry. Chiral intermediates and fine chemicals are in high demand from both the pharmaceutical and agrochemical industries for the preparation of bulk drug substances and agricultural products. The enormous potential of microorganisms and enzymes for the transformation of synthetic chemicals with high chemo-, regio-and enantioselectivities has been demonstrated. In this article, biocatalytic processes are described for the synthesis of chiral pharmaceutical intermediates.

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Enzymatic synthesis of l -6-hydroxynorleucine

Cited by 87 publications

References 17 publications

Phenyl boronic acid complexes of diols and hydroxyacids

Phenyl boronic acid complexes of diols and hydroxyacids

Guidelines for the Application of NAD(P)H Regenerating Glucose Dehydrogenase in Synthetic Processes

Biocatalytic Synthesis of Chiral Pharmaceutical Intermediates

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