General Synthesis of Industrial Cephalosporin‐Based Antibiotics Through Amidation with Tosyl Chloride as a Coupling Reagent

Pieper, Matthias; Schleich, Herbert; Gröger, Harald

doi:10.1002/ejoc.201900277

Cited by 4 publications

(3 citation statements)

References 12 publications

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“…The mixture added to ice water and separated using DCM. DCM was evaporated to furnished hepta-O-acetyl-6'-O-tosyl-sucrose [5] (5.56 g 75%), which to passed to azidation without further puri ication (Ananthalakshmi et al, 2014;Yusof and Arif in, 2016;Pieper et al, 2019).…”

Section: Tosylation Of Hepta-o-acetyl-sucrose [5]mentioning

confidence: 99%

New bio-amphiphilic structures of sucrose via amides linkages

Salman¹

2019

ijrps

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A series of four new derivatives of sucrose have been synthesized using the straightforward methodology in order to give a mono substituted analogs of sucrose at C −6 ′ of fructose moiety. The synthesis was started from the reaction of sucrose with tert-butylchlorodiphenylsilane, which is able to react with an only less steric hindrance hydroxyl group at C −6 ′ due to its bulky structure. The other hydroxyl groups were acetylated by the reaction with acetic anhydride in pyridine. Then free the hydroxyl group at C −6 ′ again by the treatment with t-butylammonium luoride in THF. The later was activated by conversion to a good leaving group via tosylation, followed by functionalized via azidation to give the precursor of the target series hepta-O-acetyl-6'-azido-sucrose. The precursor was coupled with four alkyl halides (C 12 , C 8−4 , C 14 , C 10−8 ) via Staudinger reaction to produced the target structure after deacetylating. The purity and chemical structure of the synthesized compound was con irmed by CHN elemental analysis, high-resolution mass and 1 H, 13 C NMR spectroscopy.

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Section: Tosylation Of Hepta-o-acetyl-sucrose [5]mentioning

confidence: 99%

New bio-amphiphilic structures of sucrose via amides linkages

Salman¹

2019

ijrps

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“…The object of our study is a high-yielding producer of the antibiotic cephalosporin C (CPC), strain A. chrysogenum HY (RNCM 408D), obtained as a result of the CSI program from a natural isolate, A. chrysogenum WT (ATCC 11550) [ 7 ]. A. chrysogenum is an exclusive industrial producer of CPC, which serves as a feedstock for the subsequent in vitro synthesis of cephalosporin antibiotics of the 1st–5th generations [ 33 ]. Biosynthesis of CPC in A. chrysogenum is carried out due to the functioning of two biosynthetic gene clusters (BGCs), into which, respectively, the so-called “early” and “late” genes for beta-lactam biosynthesis, transport, and regulation are assembled [ 34 ].…”

Section: Introductionmentioning

confidence: 99%

Spermidine and 1,3-Diaminopropane Have Opposite Effects on the Final Stage of Cephalosporin C Biosynthesis in High-Yielding Acremonium chrysogenum Strain

Zhgun

Eldarov

2022

IJMS

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The addition of exogenous polyamines increases the production of antibiotic cephalosporin C (CPC) in Acremonium chrysogenum high-yielding (HY) strain during fermentation on a complex medium. However, the molecular basis of this phenomenon is still unknown. In the current study, we developed a special synthetic medium on which we revealed the opposite effect of polyamines. The addition of 1,3-diaminopropane resulted in an increase in the yield of CPC by 12–15%. However, the addition of spermidine resulted in a decrease in the yield of CPC by 14–15% and accumulation of its metabolic pathway precursor, deacetylcephalosporin C (DAC); the total amount of cephems (DAC and CPC) was the same as after the addition of DAP. This indicates that spermidine, but not 1,3-diaminopropane, affects the final stage of CPC biosynthesis, associated with the acetylation of its precursor. In both cases, upregulation of biosynthetic genes from beta-lactam BGCs occurred at the same level as compared to the control; expression of transport genes was at the control level. The opposite effect may be due to the fact that N1-acetylation is much more efficient during spermidine catabolism than for 1,3-diaminopropane. The addition of spermidine, but not 1,3-diaminopropane, depleted the pool of acetyl coenzyme A by more than two-fold compared to control, which could lead to the accumulation of DAC.

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“…In addition, numerous oxime-containing compounds had strong bioactivities and moderate toxicity. In medicine and the manufacture of cephalosporin derivatives with antibacterial activity, several oximes have been used as ligands [4]. Oximes are frequently used as strong H-bond donors in supramolecular chemistry, which makes them potential participants in hydrogen bonding interactions with the protein's amino acid building blocks [5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a Series of α, β-Unsaturated Ketoximes and their Corresponding Acetate Esters

Jihad

Alkazzaz²

2022

Iraqi Journal of Science

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A series of 1,3-diarylprop-2-en-1-one oximes (7-12) were synthesized via reaction of 1,3-diarylprop-2-en-1-one (1-6) with NH2OH. HCl in dry pyridine. In order to produce the required products (13-18) as anti-isomers, these products (7–12) were then treated with acetic anhydride in dry pyridine. Different substitutes are maintained, resulting in the separation of different products in different yields The recently produced esters are thought to be useful as building blocks for the synthesis of substituted pyridines and many other nitrogen-holding complexes, which are elaborate structures in medicinal chemistry and present in a variety of pharmaceutical medications. The synthesized products were characterized and their structural details were clarified using 1H NMR spectroscopy of a representative one sample ester and oxime, (FT-IR, UV) investigations, and melting point analysis. Besides the elemental micro analysis (C, H, N) of the same samples, the suggested mechanisms for these reactions were investigated according to these calculations.

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General Synthesis of Industrial Cephalosporin‐Based Antibiotics Through Amidation with Tosyl Chloride as a Coupling Reagent

Cited by 4 publications

References 12 publications

New bio-amphiphilic structures of sucrose via amides linkages

New bio-amphiphilic structures of sucrose via amides linkages

Spermidine and 1,3-Diaminopropane Have Opposite Effects on the Final Stage of Cephalosporin C Biosynthesis in High-Yielding Acremonium chrysogenum Strain

Synthesis of a Series of α, β-Unsaturated Ketoximes and their Corresponding Acetate Esters

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