Synthesis of Erythrochelin: A Hydroxamate-Type Siderophore from Saccharopolyspora erythraea
نویسندگان
چکیده
Abstract Erythrochelin, a hydroxamate-type siderophore produced by Saccharopolyspora erythraea, is synthesized for the first time. A key building block of erythrochelin containing the 2,5-diketopiperazine ring is prepared by intramolecular cyclization of the corresponding dipeptide precursor derived from two kinds of protected δ-N-hydroxy-L-ornithines. Consecutive condensation of the building block with protected D-serine and protected δ-N-hydroxy-D-ornithine, followed by deprotection, furnishes erythrochelin.
منابع مشابه
A key developmental regulator controls the synthesis of the antibiotic erythromycin in Saccharopolyspora erythraea.
Saccharopolyspora erythraea makes erythromycin, an antibiotic commonly used in human medicine. Unusually, the erythromycin biosynthetic (ery) cluster lacks a pathway-specific regulatory gene. We isolated a transcriptional regulator of the ery biosynthetic genes from S. erythraea and found that this protein appears to directly link morphological changes caused by impending starvation to the synt...
متن کاملGenome Sequence of Saccharopolyspora erythraea D, a Hyperproducer of Erythromycin
Saccharopolyspora erythraea is a Gram-positive bacterium that can produce antibiotics. However, this microorganism must often be genetically improved for higher production before it can be used in an industrial setting. Here, we report the whole-genome sequence of the industrial hyperproducer strong mutator Saccharopolyspora erythraea strain D.
متن کاملEnhancing the effect of soybean oil refinery byproducts on erythromycin production by Saccharopolyspora erythraea
Erythromycin production is clearly enhanced by the addition of vegetable oils. However,whether this positive effect is brought about by the triglyceride or non-triglyceride fraction, isnot clear. The non-triglyceride portions of the oils accumulate in the waste during the refiningprocess leaving mainly triglycerides in the refined oil. In this research, sub-fractions of soybeanoil, including le...
متن کاملPurification and separation of holo- and apo-forms of Saccharopolyspora erythraea acyl-carrier protein released from recombinant Escherichia coli by freezing and thawing.
Saccharopolyspora erythraea acyl-carrier protein, highly expressed from a T7-based expression plasmid in Escherichia coli, can be selectively released from the cells in near-quantitative yield by a single cycle of freezing and thawing in a neutral buffer. Electrospray mass spectrometry was used to confirm that the recombinant S. erythraea acyl-carrier protein over-expressed in E. coli is presen...
متن کاملTetramic Acid Analogues Produced by Coculture of Saccharopolyspora erythraea with Fusarium pallidoroseum
Coculture of the fungus Fusarium pallidoroseum with the bacterium Saccharopolyspora erythraea was found to produce three new decalin-type tetramic acid analogues related to equisetin. The structures were determined by spectroscopic methods. The absolute configurations were established by circular dichroism spectroscopy and comparing the data with those of equisetin.
متن کامل