Biosynthesis of the Nucleoside Antibiotics

Suhadolnik, Robert J.

doi:10.1007/978-3-642-67724-3_16

Cited by 47 publications

(87 citation statements)

References 46 publications

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“…This moiety should be linked to the -NH, group of 3'-amino-3'-deoxyadenosine moiety of A201A. This moiety should be synthesized from adenosine in S. ccipreolus in a similar manner to that in S. alboiziger, as an intermediate of the puromycin biosynthetic pathway (Suhadolnik, 1981;Tercero et al, 1996), or as in Helminthosporium sp., as a final product (Chassy and Suhadolnik, 1969). In this respect, the ardl gene is next to a putative gene (ORFI) whose deduced product is practically identical to that from yur3 of the pur cluster (Barrasa et al, 1995) and which is thought to hydrolyze a 5'-phosphate group from a 3'-amino-3'-deoxyadenosine-5'-P-containing intermediate of the puromycin biosynthetic pathway (Tercero et al, 1996).…”

Section: Discussionmentioning

confidence: 99%

The Aminonucleoside Antibiotic A201A is Inactivated by a Phosphotransferase Activity from Streptomyces Capreolus NRRL 3817, the Producing Organism

Barrasa

Tercero

Jiménez

1997

European Journal of Biochemistry

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A novel resistance determinant (ard2) to the aminonucleoside antibiotic A201A was cloned from Streptomyces capreolus NRRL 3817, the producing organism, and expressed in Streptomyces lividans. Sequencing and subcloning experiments of a 3-kb fragment localized nrd2 to an ORF of 591 nucleotides. Cell-free extracts from both S. capreolus and S. lividans (ard2) were shown to phosphorylate A201A in an ATP-dependent reaction. The resulting product (P-A201A) was purified and shown to lack any detectable biological activity against a gram-positive indicator organism. Phosphorylation by Ard2 takes place on the hydroxyl group at C2 of the unsaturated hexofuranose moiety of A201A, as shown by 'H-NMR analysis of purified P-A201A. The expression of ard2 appears to be developmentally controlled. In addition to ard2, the sequenced DNA fragment contained two incomplete ORFs (2 and 5) and one complete ORF (4), which appear to determine enzymes of the A201A biosynthetic pathway. Whereas the deduced product of ORF2 did not show any similarity to proteins in data banks, those of ORF5 and ORF4 encode putative glycosyltransferase and ketoreductase activities, respectively. ard2 and these three ORFs seem to be transcribed in a single polycistronic transcript, which supports the notion that they are a part of an A201A biosynthetic gene cluster.

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Section: Discussionmentioning

confidence: 99%

The Aminonucleoside Antibiotic A201A is Inactivated by a Phosphotransferase Activity from Streptomyces Capreolus NRRL 3817, the Producing Organism

Barrasa

Tercero

Jiménez

1997

European Journal of Biochemistry

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“…The parent compound, 5-azauracil, (2), is an antimetabolite (Suhadolnik, 1970) which inhibits the biosynthesis of pyrimidine bases and thus the production of nucleic acids (Adams & Davidson, 1981), whilst 6-azauracil has also revealed antineoplastic activity in animal tumours (Swindler & Welch, 1957). Since the extensive possibilities for hydrogen bonding in the triazinedione ring system in such compounds are likely to be important in such biological activity, the structure of (1) has been determined.…”

Section: Commentmentioning

confidence: 99%

Classical Packing and Stacking in 6-Phenyl-5-azauracil

Lowe¹,

Schwalbe²

1998

Acta Crystallogr C

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“…This type of substances, namely C-aryl alditols, can be considered as acyclo-C-nucleoside analogues that by intramolecular dehydration could provide C-nucleosides; some of the latter, either natural or synthetic, have been reported to have a broad range of useful antitumor, antifungal and antibiotic properties, thus encouraging the development of methodologies toward this class of products. [8][9][10][11] Besides, the C-aryl alditol substructure is also present in some natural products, like the 5-(4-aminophenyl)-1,2,3,4-tetrahydroxypentane moiety of methanopterin, a cofactor involved in the biological reduction of CO 2 to CH 4 .…”

Section: Introductionmentioning

confidence: 99%

New C-aryl alditols from Diels-Alder adducts of sugar nitroalkenes

Araújo¹,

Baños²,

Gil³

et al. 2008

Arkivoc

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2-Nitro-, 2-amino-and 2-acetamido-1-(penta-O-acetylpentitol-1´-yl)benzenes were prepared using previously reported Diels-Alder cycloadducts obtained from sugar-derived nitroalkenes with D-galacto and D-manno configurations as starting materials. Deacetylation and oxidative cleavage of the sugar side-chain of nitrobenzene pentitol peracetates yielded nitrobenzaldehydes. From 2-nitro-1-(D-galacto-pentitol-1´-yl)benzene also 1´,4´-and 2´,5´-anhydro derivatives were synthesized.

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Biosynthesis of the Nucleoside Antibiotics

Cited by 47 publications

References 46 publications

The Aminonucleoside Antibiotic A201A is Inactivated by a Phosphotransferase Activity from Streptomyces Capreolus NRRL 3817, the Producing Organism

The Aminonucleoside Antibiotic A201A is Inactivated by a Phosphotransferase Activity from Streptomyces Capreolus NRRL 3817, the Producing Organism

Classical Packing and Stacking in 6-Phenyl-5-azauracil

New C-aryl alditols from Diels-Alder adducts of sugar nitroalkenes

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