A novel dioxabicyclo[3.3.1]nonane, a key intermediate in the synthesis of erythronolide B seco-acid

1994 ◽  
Vol 50 (9) ◽  
pp. 1467-1469 ◽  
Author(s):  
V. M. Lynch ◽  
W. C. Lee ◽  
S. F. Martin ◽  
B. E. Davis
Keyword(s):  
Erythronolide B

ChemInform Abstract: TOTAL SYNTHESIS OF ERYTHROMYCINS. 4. TOTAL SYNTHESIS OF ERYTHRONOLIDE B

1978 ◽  
Vol 9 (42) ◽  
Author(s):  
E. J. COREY ◽  
S. KIM ◽  
S. YOO ◽  
K. C. NICOLAOU ◽  
L. S. JUN. MELVIN ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Erythronolide B

Erythronolide B: Analysis of the synthesis pathway proposed by the Lilith program

1992 ◽  
Vol 111 (6) ◽  
pp. 297-303 ◽  
Author(s):  
Luca Baumer ◽  
Ilaria Compagnari ◽  
Giordano Sala ◽  
Guido Sello
Keyword(s):  
Erythronolide B

scholarly journals Identification and Expression of Genes Involved in Biosynthesis of l-Oleandrose and Its Intermediatel-Olivose in the Oleandomycin ProducerStreptomyces antibioticus

2000 ◽  
Vol 44 (5) ◽  
pp. 1266-1275 ◽  
Author(s):  
Ignacio Aguirrezabalaga ◽  
Carlos Olano ◽  
Nerea Allende ◽  
Leticia Rodriguez ◽  
Alfredo F. Braña ◽  
...  
Keyword(s):  
Sequence Analysis ◽  
Gene Cluster ◽  
Enzyme Activities ◽  
Open Reading Frames ◽  
Streptomyces Antibioticus ◽  
Recombinant Strains ◽  
Expression Of Genes ◽  
Streptomyces Albus ◽  
Erythronolide B ◽  
Reading Frames

ABSTRACT A 9.8-kb DNA region from the oleandomycin gene cluster inStreptomyces antibioticus was cloned. Sequence analysis revealed the presence of 8 open reading frames encoding different enzyme activities involved in the biosynthesis of one of the two 2,6-deoxysugars attached to the oleandomycin aglycone:l-oleandrose (the oleW, oleV,oleL, and oleU genes) andd-desosamine (the oleNI and oleTgenes), or of both (the oleS and oleE genes). AStreptomyces albus strain harboring the oleG2glycosyltransferase gene integrated into the chromosome was constructed. This strain was transformed with two different plasmid constructs (pOLV and pOLE) containing a set of genes proposed to be required for the biosynthesis of dTDP-l-olivose and dTDP-l-oleandrose, respectively. Incubation of these recombinant strains with the erythromycin aglycon (erythronolide B) gave rise to two new glycosylated compounds, identified asl-3-O-olivosyl- andl-3-O-oleandrosyl-erythronolide B, indicating that pOLV and pOLE encode all enzyme activities required for the biosynthesis of these two 2,6-dideoxysugars. A pathway is proposed for the biosynthesis of these two deoxysugars in S. antibioticus.

Total synthesis of erythronolide B. 1. Skeleton assembly in (C9C13) + (C7C8) + (C1C6) sequence.

1987 ◽  
Vol 28 (33) ◽  
pp. 3835-3838 ◽  
Author(s):  
A.F. Sviridov ◽  
M.S. Ermolenko ◽  
D.V. Yashunsky ◽  
V.S. Borodkin ◽  
N.K. Kochetkov*
Keyword(s):  
Total Synthesis ◽  
Erythronolide B

Synthesis of brefeldin A, carpaine, vertaline, and erythronolide B from nonmacrocyclic precursors

1975 ◽  
Vol 97 (3) ◽  
pp. 654-655 ◽  
Author(s):  
E. J. Corey ◽  
K. C. Nicolaou ◽  
Lawrence S. Melvin
Keyword(s):  
Brefeldin A ◽  
Erythronolide B

Synthesis of macrolide antibiotics. Communication 8. Synthesis of acyclic forms of C9-C13 fragment of erythronolide B

1985 ◽  
Vol 34 (5) ◽  
pp. 1066-1071
Author(s):  
A. F. Sviridov ◽  
D. V. Yashunskii ◽  
M. S. Ermolenko ◽  
V. S. Borodkin ◽  
N. K. Kochetkov
Keyword(s):  
Macrolide Antibiotics ◽  
Erythronolide B

scholarly journals Selected Derivatives of Erythromycin B-In Silico and Anti-Malarial Studies

Materials ◽  
2021 ◽  
Vol 14 (22) ◽  
pp. 6980
Author(s):  
Pranab K. Bhadra ◽  
Rachael N. Magwaza ◽  
Niroshini Nirmalan ◽  
Sally Freeman ◽  
Jill Barber ◽  
...  
Keyword(s):  
Molecular Docking ◽  
In Silico ◽  
Bacterial Agent ◽  
Ic50 Values ◽  
Exit Tunnel ◽  
Erythromycin A ◽  
Erythronolide B ◽  
In Silico Molecular Docking ◽  
Derivatives Of

Erythromycin A is an established anti-bacterial agent against Gram-positive bacteria, but it is unstable to acid. This led to an evaluation of erythromycin B and its derivatives because these have improved acid stability. These compounds were investigated for their anti-malarial activities, by their in silico molecular docking into segments of the exit tunnel of the apicoplast ribosome from Plasmodium falciparum. This is believed to be the target of the erythromycin A derivative, azithromycin, which has mild anti-malarial activity. The erythromycin B derivatives were evaluated on the multi-drug (chloroquine, pyrimethamine, and sulfadoxine)-resistant strain K1 of P. falciparum for asexual growth inhibition on asynchronous culture. The erythromycin B derivatives were identified as active in vitro inhibitors of asexual growth of P. falciparum with low micro-molar IC50 values after a 72 h cycle. 5-Desosaminyl erythronolide B ethyl succinate showed low IC50 of 68.6 µM, d-erythromycin B 86.8 µM, and erythromycin B 9-oxime 146.0 µM on the multi-drug-resistant K1 of P. falciparum. Based on the molecular docking, it seems that a small number of favourable interactions or the presence of unfavourable interactions of investigated derivatives of erythromycin B with in silico constructed segment from the exit tunnel from the apicoplast of P. falciparum is the reason for their weak in vitro anti-malarial activities.

scholarly journals Multiplexed Integrating Plasmids for Engineering of the Erythromycin Gene Cluster for Expression in Streptomyces spp. and Combinatorial Biosynthesis

2015 ◽  
Vol 81 (24) ◽  
pp. 8402-8413 ◽  
Author(s):  
Bahgat Fayed ◽  
David A. Ashford ◽  
Amal M. Hashem ◽  
Magdy A. Amin ◽  
Omaima N. El Gazayerly ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Polyketide Synthase ◽  
Gene Cassette ◽  
Antibiotic Activity ◽  
Combinatorial Biosynthesis ◽  
Liquid Chromatography Mass Spectrometry ◽  
Content Type ◽  
Streptomyces Spp ◽  
Erythronolide B ◽  
Close Relatives

ABSTRACTBacteria in the genusStreptomycesand its close relatives are prolific producers of secondary metabolites with antibiotic activity. Genome sequencing of these bacteria has revealed a rich source of potentially new antibiotic pathways, whose products have never been observed. Moreover, these new pathways can provide novel genes that could be used in combinatorial biosynthesis approaches to generate unnatural analogues of existing antibiotics. We explore here the use of multiple orthologous integrating plasmid systems, based on theint/attPloci from phages TG1, SV1, and ϕBT1, to express the polyketide synthase (PKS) for erythromycin in a heterologousStreptomyceshost.Streptomycesstrains containing the three polyketide synthase geneseryAI,eryAII, anderyAIIIexpressed from three different integrated plasmids produced the aglycone intermediate, 6-deoxyerythronolide B (6-dEB). A further pair of integrating plasmids, both derived from the ϕC31int/attPlocus, were constructed carrying a gene cassette for glycosylation of the aglycone intermediates, with or without the tailoring gene,eryF, required for the synthesis of erythronolide B (EB). Liquid chromatography-mass spectrometry of the metabolites indicated the production of angolosaminyl-6-dEB and angolosaminyl-EB. The advantages of using multiplexed integrating plasmids for engineering expression and for combinatorial biosynthesis were demonstrated.

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