Isolation and characterization of sporeamicin B.

Morishita, Atsuki; Murofushi, Sakae; Ishizawa, Kenya; Mutoh, Naoki; Yaginuma, Satoshi

doi:10.7164/antibiotics.45.809

Cited by 6 publications

(4 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…C-3-and C-5-O-glycosylation is the most predominate among 14-membered macrolides, but C-6-, C-7-, C-9-and, in one case (CP 64537, containing either 140 or 170c), 640 C15-O-glycosylation has also been observed. Reminiscent of classical 12-and 16-membered macrolides, 14-membered macrolides (including erythromycins, 634,[641][642][643] megalomycin, 644,645 picromycin, 646 oleandomycins, 647 sporeamicins; [648][649][650][651] Sections 12.1 and 12.3) typically contain the common C-5 b-D-desosamine (177a). The corresponding N-desmethyl-b-Ddesosamine (177b) 634 is also found at this position as exemplified by the cineromycins [which also contain a C7 a-D-glucose (18)] 652 C-3-O-glycosylation is also prevalent, albeit less important for bioactivity, and includes 3-O-methyl-a-L-mycarose (also known as a-L-cladinose, 90b), 634,648,653,654 a-L-mycarose (90a; as observed in CP64593, 640 sporeamicin-C 650 or the 2-norerythromycins deriving from pathway engineering), 655 or the C-3 0 /C-4 0 -modified form (90c/90d, Fig.…”

Section: -Member Macrolidesmentioning

confidence: 99%

A comprehensive review of glycosylated bacterial natural products

et al. 2015

View full text Add to dashboard Cite

A systematic analysis of all naturally-occurring glycosylated bacterial secondary metabolites reported in the scientific literature up through early 2013 is presented. This comprehensive analysis of 15 940 bacterial natural products revealed 3426 glycosides containing 344 distinct appended carbohydrates and highlights a range of unique opportunities for future biosynthetic study and glycodiversification efforts.

show abstract

Section: -Member Macrolidesmentioning

confidence: 99%

A comprehensive review of glycosylated bacterial natural products

et al. 2015

View full text Add to dashboard Cite

show abstract

“…erythromycin A: 2) containing a 9,12-anhydro moiety. Sporeamycin B (3) [4] and C (4) [5] have also been isolated. In 1996, 6-deoxysporeamycin A (5) [6] was derived from 6-deoxyerythromycin A.…”

mentioning

confidence: 98%

“…Tin-aldol-reaction with an excess of methacrolein gave a mixture of diastereoisomeric allylic alcohols from which the pure syn aldol ()-11 could be isolated in 87% yield. Treatment of ()-11 with Et 2 BOMe, followed by NaBH 4 in THF/MeOH at À 788 [12] furnished a diol that was transformed in situ into its acetonide under standard conditions, the ozonolysis of which provided ()-8 in an overall yield of 66% (Scheme 1).…”

mentioning

confidence: 99%

“…This 2 Cu as a catalyst [23], furnishing the alkene ()-18 in 75% yield. Ozonolysis followed by reductive workup with Me 2 S and with NaBH 4 The major sulfoxide ()-24 was used in the condensation with the methyl ketone ()-8 (Scheme 3). The conjugate base of ()-24, obtained by treatment with LDA and N,N,N',N'-tetramethylethylenediamine (TMEDA) in THF at À 788, reacted with ()-8 to give a mixture from which ()-26 was isolated in 40% yield together with 35% of the recovered ketone ()-8.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Total Asymmetric Synthesis of a New 9,12-Anhydroerythronolide Aglycone

Gerber‐Lemaire

Ainge

Glanzmann

et al. 2002

HCA

View full text Add to dashboard Cite

Two novel, potentially antimicrobial erythronolide aglycon analogs ((À)-9 and (À)-30, respectively), which incorporate a large number of contiguous stereogenic centers, have been prepared by multistep synthesis from simple chirons. The chemistry presented demonstrates the power of the so-called −naked sugars of the second generation× approach. As for the sporeamicins, our macrolides are 9,12-anhydroerythronolides, yet presenting a higher degree of complexity due to additional functional groups.

show abstract

Antibiotics, Macrolides

Kirst

2001

Kirk-Othmer Encyclopedia of Chemical Technology

View full text Add to dashboard Cite

Macrolide antibiotics are well‐established antimicrobial agents in clinical and veterinary medicine. These agents can be administered orally and are generally used to treat infections in the respiratory tract, skin and soft tissues, and genital tract caused by gram‐positive organisms, Mycoplasma species, and certain susceptible gram‐negative and anaerobic bacteria. The macrolide class is large and structurally diverse. Macrolides are produced by fermentation of soil microorganisms. Additionally, structural modifications using both chemical and microbiological means have yielded biologically active semisynthetic derivatives. The term macrolide was introduced to denote the class of substances produced by Streptomyces species containing a macrocyclic lactone. Traditional macrolide antibiotics are divided into three families according to the size of the aglycone, which can be a 12‐, 14‐, or 16‐membered ring. Naturally occurring 14‐membered macrolides include erythromycin A and erythromycin B, as well as others. Erythromycin has been the principal subject of modification of 14‐membered macrolides; its semisynthetic derivatives include erythromycin ethyl succinate, roxithromycin, clarithromycin, azithromycin, dirithromycin, and others. More recently, the ketolide family has been discovered that exhibits activity against certain macrolide‐resistant strains, from which telithromycin and ABT‐773 are in clinical trials. The 16‐membered macrolides are divided into leucomycin‐ and tylosin‐related groups, which differ in the substitution pattern of their aglycones. Natural products include josamycin (leucomycin A 3 ), spiramycin, and others. The most prominent member of the second group is tylosin, an important veterinary antibiotic. Semisynthetic 16‐membered macrolides include miokamycin, rokitamycin, AIV‐tylosin, and tilmicosin. The advent of molecular biology has opened new possibilities for producing novel macrolides by genetic manipulations of biosynthetic pathways from macrolide‐producing microorganisms (combinatorial biosynthesis) that complement traditional chemical and microbiological approaches. Macrolides inhibit growth of gram‐positive bacteria, Mycoplasma species, and certain gram‐negative and anaerobic bacteria. Susceptible gram‐positive bacteria include many species of Staphylococcus and Streptococcus ; susceptible gram‐negative bacteria include Bordetella pertussis, Legionella pneumophila, Moraxella catarrhalis , Campylobacter sp., Chlamydia sp., and Helicobacter pylori . Some derivatives have shown promising activity against non‐tuberculous mycobacteria. Macrolides inhibit growth of bacteria by inhibiting protein synthesis on ribosomes. Bacterial resistance to macrolides is often accompanied by cross‐resistance to lincosamide and streptogramin B antibiotics (MLS‐resistance). Bacterial resistance to antibiotics usually results from modification of a target site, enzymatic inactivation, or reduced uptake into or increased efflux from bacterial cells. The principal side effects of macrolides are gastrointestinal problems, such as pain, indigestion, diarrhea, nausea, and vomiting. Macrolide antibiotics are used clinically to treat infections resulting from susceptible organisms in the upper and lower respiratory tract, skin and soft tissues, and genital tract. They are generally used orally, although they can be given intravenously. Macrolides are regarded as among the safest of antibiotics. A few macrolides are used in veterinary medicine, such as tylosin and tilmicosin which are used to control respiratory diseases and other infections in poultry, pigs, and cattle.

show abstract

Isolation and characterization of sporeamicin B.

Abstract: Communications to the Editor ISOLATION AND CHARACTERIZATION OF SPOREAMICIN B Sir: Sporeamicin A is a 14-membered macrolide antibiotic produced by Saccharopolyspora sp. L53-18, which has strong antibacterial activity against Gram-positive bacteria.x~4) During the

Cited by 6 publications

References 3 publications

A comprehensive review of glycosylated bacterial natural products

A comprehensive review of glycosylated bacterial natural products

Total Asymmetric Synthesis of a New 9,12-Anhydroerythronolide Aglycone

Antibiotics, Macrolides

Contact Info

Product

Resources

About