Antibiotics nucleoside type

Purinethol mercaptopurine. puromycin ban, inn, usan] (puromycin hydrochloride [USAN] NSC 3055 CL 16536 antibiotic CL 16536 CL 13900 3123L P 638 antibiotic CL 13900 antibiotic 3123L antibiotic P 638) is a nucleoside-type ANTIBIOTIC isolated from Streptomyces alboniger. It has anticancer and ANTITRYPANOSOMAL activity, puromycin hydrochloride puromycin. p-xylotocopherol p-tocopherol. 

In various fungi, including those of Basidiomycotina, numerous nucleoside-type metabolites and related free bases have been found (369). Apart from the typical components that are structural units of nucleic acid chains, like adenosine from Amanita muscaria (9), some of the nucleoside analogs apparently deserve special interest because of their biological and pharmaceutical activities, which eu-e usually induced by a slight difference in structural features. In addition, the role played by such nucleoside antibiotics in protein and nucleic acid biosynthesis might be of great importance. 

Streptothricins. A mixture of antibiotics of the nucleoside type first isolated in 1942 by Waksman and Woodruff from streptomycetes. S. were first considered to be a uniform substance and given the name S. F. The mixture was later found to consist of several, frequently occurring compounds that differ in the number of /3-lysine units in the side chain. 

C17H23N7O5 405.413 Nucleoside-type antibiotic. Degradn. prod, of Blasticidin S by microbes such as Pseudomonas marginalis, Pseudomonas avails and Fusarium oxysporum. Possesses antitumour activity. Sol. H2O fairly sol. MeOH poorly sol. Mc2CO, hexane. 

C9H15N3O5 245.235 Nucleoside-type antibiotic. Obt. from Streptomyces platensis var. clarensis and Micromonospora melanogenes. Antiviral agent, useful against herpes simplex. Also active against grampositive and -negative bacteria. Needles. Sol. H2O. 

C10H13N5O4 267.244 Nucleoside-type antibiotic. Prod, by Nocardia interforma, Streptomyces lavendulae and Streptomyces gunmaen-sis. Shows limited antibacterial activity but possesses antitumour and antiviral props. Cryst. Sol. MeOH, H2O, acids, bases fairly sol. EtOH poorly sol. Me2CO, hexane. 

C20H23N3O12 497.415 Nucleoside-type antibiotic. Main component of blue pigment Amylocyanin from Streptomyces coelicolor. Also isol. from Arthrobacter polychromogenes. Sol. H2O, DMF poorly sol. MeOH, hexane. Mp 330°. Minor components of Indochrome are the isomers Indochrome BI which has one a-D-ribopyranosyl residue, and Indochrome BII which has one P-D-ribofuranosyl residue. 255 340 586 (H2O) (Berdy). 255 340 596 (pH 13 buffer) (Berdy). 240 255 570 (pH 2 buffer) (Berdy). 

C,7H2oN20 6 348.355 Nucleoside-type antibiotic. Metab. from Streptomyces hygroscopicus. Weakly active against gram-negative bacteria. Amorph. powder + V2H2O. Sol. MeOH, butanol. 

Nucleoside-type antibiotic. Metab. of Streptomyces tendae and from Streptomyces cacaoi. Antifungal agent which also inhibits chitin biosynth. 

Nucleoside-type antibiotic. Produced by Streptomyces calms. Antitrypanosomal which inhibits protein synth. Cryst. 

Nucleoside-type antibiotic. Isol. from Streptomyces tanesashinensis, Strepto-myces hygroscopicus and Pseudomonas paucimobilis. Antibiotic active against gram-positive and gram-negative bacteria. 

C11H13N3O5 267.241 Nucleoside-type antibiotic. Struct, revised in 1992. Prod, by Streptomyces albus. 

C11H18N2O7 290.272 Nucleoside-type antibiotic. Prod, by Rhizobium loti on Lotus spp. Cryst. (MeOH). 

Nucleoside-type antibiotic. Synthetic. Antineoplastic and antiviral agent. Cryst. (2-propanol). Mp 131-133 . 

Nucleoside-type antibiotic complex. Should not be confused with the antibiotic from S. fradiae and now called Neomycin A (see Neomycin A, N-22). Struct, revised in 1982. Isol. from Streptomyces sp. Shows broad spectrum of activity, but acutely toxic. 

Sulfamates (0-substituted-, N-substituted-, or di-/tri-substituted derivatives of sulfamic acid) have been used in the design of many types of therapeutic agents such as antibiotics, nucleoside/nucleotide human immunodeficiency virus (HTV) reverse transcriptase inhibitors, HIV protease inhibitors (Pis), anti-cancer drugs (steroid sulfatase and carbonic anhydrase inhibitors), anti-epileptic drugs, and weight loss drugs. 

Asymmetric induction in the aldol reaction of enolsilane and metal enolate nucleophiles with yS-substituted aldehydes gives rise to both excellent yields and good diastereoselectivities (equation 128)507. The best diastereoselectivity was obtained using a trimethylsilyl enolate in the presence of boron trifluoride-etherate (92 8 anti. syn). The key step in the synthesis of the N-terminal amino acid analogue of nikkomycin B and Bx (nucleoside peptide antibiotics) has been performed using this type of methodology508. 

Scheme 1. Examples of naturally occurring nucleoside antibiotics containing an extended carbohydrate-type core structure...

The first total synthesis of the nucleoside antibiotic herbicidin B was accomplished in the laboratory of A. Matsuda. The key step was a novel aldol-type C-glycosidation reaction promoted by Sml2 between a 1-phenylthio-2-ulose derivative and a 1- 3-D-xylosyladenine-5 -aldehyde derivative. During the preparation of the phenylthio sugar subunit, the Moffatt oxidation was applied to convert the primary alcohol to the corresponding aldehyde, which was immediately oxidized with PDC in DMF/MeOH to the methyl ester. The reaction conditions were completely compatible with the silyl protecting group as well as the thioacetal functionality. 

Only two types of heterocycles that belong to this group have been obtained from sugars they are the antihelminthic and and-infectious bengamides as well as the lipid-containing nucleoside antibiotics liposidomycins. This is why this chapter is the shortest one in the book. 

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