New tetrazole-1-acetic acid esters for enzymatic synthesis of cefazolin

Kostadinov, M.; Nikolov, Al. T.; Tsoneva, N.; Petkov, Nikolay

doi:10.1007/bf02921833

Cited by 16 publications

(4 citation statements)

References 7 publications

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“…Isopropyl-2-aminoacetate hydrochloride was synthesized according to the literature, 2-(5-bromo-1 H -tetrazol-1-yl)ethanol ( 8a ) according to Bayes, and isopropyl 2-(1 H -tetrazol-1-yl)acetate ( 7b ) according to the literature …”

Section: Methodsmentioning

confidence: 99%

Synthesis of Functionalized Tetrazenes as Energetic Compounds

2009

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1,4-Bis[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]-1,4-dimethyl-2-tetrazene (12a), 1,4-bis[1-isopropoxycarbonylmethyl-1H-tetrazol-5-yl]-1,4-dimethyl-2-tetrazene (12b), and 1,4-bis[1-carboxymethyl-1H-tetrazol-5-yl]-1,4-dimethyl-2-tetrazene (13) have been synthesized as new nitrogen-rich compounds. The tetrazenes were obtained by oxidation of the corresponding tetrazolylhydrazines using bromine. Moreover, a new method to prepare tetrazolylhydrazines in high yield using 5-bromotetrazoles has been developed. 12a, 12b, and 13 were characterized using vibrational spectroscopy (IR, Raman), mass spectrometry, and multinuclear NMR spectroscopy. The crystal structures of 12a, 12b, and 13 were determined using single crystal X-ray diffraction. Furthermore, the energetic properties of 12a, 12b, and 13 have been investigated using DSC and bomb calorimetric measurements. The sensitivity data toward impact and friction has been determined using BAM methods.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Functionalized Tetrazenes as Energetic Compounds

2009

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“…Kostadinov et al published the synthesis of cefazolin from 3-[5-methyl-1,3,4-thiadiazol-2yl]-7-ACA (M-7-ACA) and n-butyl tetrazole-1-acetic acid ester (BTAA, Scheme 20). 48 Reactions were run with PcA immobilized on EUPERGIT C in a batch reactor (35 °C, pH 6.8, pH-stat, 4 equiv BTAA, water as solvent, mg scale). Each cycle took approximately 165 min.…”

Section: D Burkholderia Cepaciamentioning

confidence: 99%

“…Basically, the amino group of the β-lactam nucleus, for example, 6-APA or 7-ACA, is reacted with novel carboxylic acid derivatives. Kostadinov et al published the synthesis of cefazolin from 3-[5-methyl-1,3,4-thiadiazol-2-yl]-7-ACA (M-7-ACA) and n -butyl tetrazole-1-acetic acid ester (BTAA, Scheme ) . Reactions were run with PcA immobilized on EUPERGIT C in a batch reactor (35 °C, pH 6.8, pH-stat, 4 equiv BTAA, water as solvent, mg scale).…”

Section: Biotransformations With Eupergitmentioning

confidence: 99%

EUPERGIT Oxirane Acrylic Beads: How to Make Enzymes Fit for Biocatalysis

Böller

Meier

Menzler

2002

Org. Process Res. Dev.

163

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Enzyme recycling is essential for the development of large-scale enzyme-catalyzed biotransformations. Recycling is most convenient using enzymes immobilized on solid supports. Although immobilization on solid supports has been pursued since the 1950s, there are no general rules for selecting the best support for a given application. The commercial products EUPERGIT C and EUPERGIT C 250 L have been used for a wide variety of different enzymes and reactions. The present review draws up a comprehensive application profile of both EUPERGIT carriers. The reader gets (a) examples of biotransformations using oxidoreductases, transferases, hydrolases and lyases immobilized on EUPERGIT; (b) key data of the biotransformations, i.e., scale, yield, purity, and enantiomeric excess; (c) efficiency of the immobilization (% immobilized activity); (d) where appropriate, operational stability of the immobilized enzyme preparations, that is, number of cycles, residual activity; (e) specific advantages of the immobilized enzyme over the free enzyme apart from enzyme recycling, for example, improved stability and selectivity. Thus, the present review can serve as a guideline when selecting a resin for enzyme immobilization. Literature published between 1985 and 2000 is covered.

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“…Penicillin G acylase (PGA) is used as a catalyst for the enzymatic semisyntheses of several penicillins and cephalosporins (11,(15)(16)(17)21). An immobilized derivative of PGA is usually employed to ensure suitable enzyme stability and consequently enzyme recovery and reuse (7,10).…”

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confidence: 99%