Berninamycin. I. The structure of berninamycinic acid

Liesch, Jerrold M.; McMillan, Joyce A.; Pandey, Ramesh C.; Paul, Iain C.; Rinehart, Kenneth L.; Reusser, Fritz

doi:10.1021/ja00417a082

Cited by 21 publications

(8 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Promoinducin was isolated by Seto et al in 1995 from Streptomyces sp . Sulfomycins were isolated from Streptomyces viridochromogenes by Egawa et al in 1969. , Berninamycin was isolated by Liesch et al from Streptomyces bernensis in 1976. − So far, none of these compounds has been synthesized.…”

Section: Thiazolyl Peptidesmentioning

confidence: 99%

Heteroaryl Rings in Peptide Macrocycles

2019

View full text Add to dashboard Cite

This Review is devoted to the chemistry of macrocyclic peptides having heterocyclic fragments in their structure. These motifs are present in many natural products and synthetic macrocycles designed against a particular biochemical target. Thiazole and oxazole are particularly common constituents of naturally occurring macrocyclic peptide molecules. This frequency of occurrence is because the thiazole and oxazole rings originate from cysteine, serine, and threonine residues. Whereas other heteroaryl groups are found less frequently, they offer many insightful lessons that range from conformational control to receptor/ligand interactions. Many options to develop new and improved technologies to prepare natural products have appeared in recent years, and the synthetic community has been pursuing synthetic macrocycles that have no precedent in nature. This Review attempts to summarize progress in this area.

show abstract

Section: Thiazolyl Peptidesmentioning

confidence: 99%

Heteroaryl Rings in Peptide Macrocycles

2019

View full text Add to dashboard Cite

show abstract

“…Hydrolysis of berninamycin in aqueous acid at 110' gives berninamycinic acid (15), u-lioce structure was established by X-ray diffraction (57). Hydrolysis of berninamycin in aqueous acid at 110' gives berninamycinic acid (15), u-lioce structure was established by X-ray diffraction (57).…”

Section: -M E T H Y L Sallcy Lic Acidmentioning

confidence: 99%

“…More recently still, questions have been raised concerning the nature of the most unusual portion of berninamycin, the polycyclic unit, which we have called berninamycinic acid. Hydrolysis of berninamycin in aqueous acid at 110°g ives berninamycinic acid (15), whose structure was established by X-ray diffraction (57). The structural unit corresponding to 15 in 14 would be a (fig.…”

mentioning

confidence: 99%

Recent Biosynthetic Studies on Antibiotics

Rinehart¹,

Weller²,

Pearce³

1980

J. Nat. Prod.

View full text Add to dashboard Cite

During recent years our re-earch group ha. been engaged in biobynthetic studies dealing Tt-ith antibiotic, of two different sort>. In a continuing qtudy we have investigated the biosynthetic origin. of the very important aminocyclitol antibiotics, which include gentamicin. neomycin, streptomycin, -pectinoniycin, etc. This topic has been reriened extensively vithin the past \- ear (1. 2 . 3). E-AMINOACETOPHENONEFIG. 2. Blternative biosynthetic pathxays t o m-aminoacetophenone.

show abstract

“…Berninamycins A-D were originally isolated from Streptomyces bernensis [10][11][12][13] and recently we reported identification of berninamycin A (Fig. 1) from different species, S. atroolivaceus 14 .…”

Section: Introductionmentioning

confidence: 99%

Isolation of New Thiopeptide Berninamycin E from Streptomyces atroolivaceus

Kodani¹,

Ninomiya²

2013

Asian J. Chem.

View full text Add to dashboard Cite

Thiopeptide antibiotic, berninamycins A, was originally isolated from Streptomyces bernensis. In this report, new berninamycin analogue named berninamycin E was isolated using several procedures using column chromatography from acetone extract of S. atroolivaceus NBRC 12741. High resolution ESI-MS spectrum data determined the molecular fomula of berninamycin E as C51H53N15O15S. The structure of berninamycin E was determined using NMR and MS spectra.

show abstract

Berninamycin. I. The structure of berninamycinic acid

Cited by 21 publications

References 0 publications

Heteroaryl Rings in Peptide Macrocycles

Heteroaryl Rings in Peptide Macrocycles

Recent Biosynthetic Studies on Antibiotics

Isolation of New Thiopeptide Berninamycin E from Streptomyces atroolivaceus

Contact Info

Product

Resources

About