title: Biosynthesis of 4-aminoheptose 2-epimers, core structural components of the septacidins and spicamycins.
abstract: Septacidins and spicamycins are acylated 4-aminoheptosyl-β-N-glycosides produced by Streptomyces fimbriatus and S. alanosinicus, respectively. Their structures are highly conserved, but differ in the stereochemistry of the 4-aminoheptosyl residues. The origin of this stereochemistry is unknown, but is presumably because of the difference in their biosynthetic pathways. We have synthesized the septacidin 4-aminoheptose to verify the difference between septacidin and spicamycin. Isotopic enrichment studies were undertaken using S. fimbriatus, and show that the septacidin heptose is derived from the pentose phosphate pathway. This indicates conserved pathways leading to the biosynthesis of 4-amino-4-deoxy-L-gluco-heptose or 4-amino-4-deoxy-L-manno-heptose.
authors.affiliation: USDA-ARS, National Center for Agricultural Utilization Research, Peoria, IL, USA.
authors.forename: Neil P J
authors.initials: NP
authors.lastname: Price
authors.affiliation: Department of Chemistry, Wayne State University, Detroit, MI, USA.
authors.forename: Takayuki
authors.initials: T
authors.lastname: Furukawa
authors.affiliation: Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, China.
authors.forename: Fang
authors.initials: F
authors.lastname: Cheng
authors.affiliation: Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, China.
authors.forename: Jianzhao
authors.initials: J
authors.lastname: Qi
authors.affiliation: Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, China.
authors.forename: Wenqing
authors.initials: W
authors.lastname: Chen
authors.affiliation: Department of Chemistry, Wayne State University, Detroit, MI, USA.
authors.forename: David
authors.initials: D
authors.lastname: Crich
mesh_terms: D000903:Antibiotics, Antineoplastic / Q000096:biosynthesis*; D004926:Escherichia coli / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D005998:Glycine / Q000737:chemistry; D006539:Heptoses / Q000096:biosynthesis / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011684:Purine Nucleosides / Q000096:biosynthesis; D012997:Solvents; D021241:Spectrometry, Mass, Electrospray Ionization; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013302:Streptomyces / Q000737:chemistry
chemical_list: D000903:Antibiotics, Antineoplastic; D006539:Heptoses; D007202:Indicators and Reagents; D011684:Purine Nucleosides; D012997:Solvents; C015502:septacidin; D005998:Glycine