ChemInform Abstract: METABOLITES OF MICROORGANISMS. 182. STRUCTURE ELUCIDATION OF THE NUCLEOSIDE ANTIBIOTIC NIKKOMYCIN X

Hagenmaier, Hanspaul; Keckeisen, Adelinde; Zaehner, H.; Koenig, W. A.

doi:10.1002/chin.198005382

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“…One such family is the high-carbon sugar nucleosides, which are modified at C-5′ of the parent ribose to generate furanosides containing 6–11 contiguous carbons. This family includes: C 6 -furanosyl nucleosides such as capuramycins A-500359s (Muramatsu et al ., 2003) and A-503083s (Muramatsu et al ., 2004), polyoxins (Isono et al ., 1965), and nikkomycins (Hagenmaier et al ., 1979); C 7 -furanosyl nucleosides such as A-90289s (Fujita et al ., 2011), caprazamycins (Igarashi et al ., 2005) liposidomycins (Ubukata et al ., 1992), muraymycins (McDonald et al , 2002), and FR-900453 (Ochi et al , 1989); C 8 -furanosyl nucleosides such as griseolic acids (Takahashi et al , 1985), octosyl acids (Isono et al ., 1975), and ezomycins (Sakata et al ., 1975); the C 10 -furanosyl nucleoside sinefungin (Boeck et al ., 1973); and the C 11 -furansoyl nucleosides herbicidins (Haneishi et al ., 1976) and tunicamycins (Takatsuki et al ., 1971) (representative structures are shown in Figure 1). …”

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confidence: 99%

Fe(II)-Dependent, Uridine-5′-Monophosphate α-Ketoglutarate Dioxygenases in the Synthesis of 5′-Modified Nucleosides

Yang¹,

Unrine²,

Nonaka³

et al. 2012

Methods in Enzymology

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Several nucleoside antibiotics from various actinomycetes contain a high-carbon sugar nucleoside that is putatively derived via C-5′-modification of the canonical nucleoside. Two prominent examples are the 5′-C-carbamoyluridine-containing and 5′-C-glycyluridine-containing nucleosides, both families of which were discovered using screens aimed at finding inhibitors of bacterial translocase I involved in the assembly of the bacterial peptidoglycan cell wall. A shared open reading frame was identified whose gene product is similar to enzymes of the non-haem, Fe(II)- and a-ketoglutarate-dependent dioxygenases. The enzyme LipL from the biosynthetic pathway for A-90289, a 5′-C-glycyluridine-containing nucleoside, was functionally characterized as UMP:α-ketoglutarate dioxygenase, providing the enzymatic imperative for the generation of a nucleoside-5′-aldehdye that serves as a downstream substrate for an aldol or aldol-type reaction leading to the high-carbon sugar scaffold. The functional assignment of LipL and the homologous enzymes—including bioinformatic analysis, iron detection and quantification, and assay development for biochemical characterization—is presented herein.

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