Macrolide antibiotics from Streptomyces

A Arisawa, N Kawamura, H Tsunekawa, K Okamura, H Tone, R Okamoto. Cloning and nucleotide sequences of two genes involved in the 4"-0-acylation of macrolide antibiotics from Streptomyces thermotolerans. Biosci Biotechnol Biochem 57 2020-2025, 1993. 

Tacrolimus is a macrolide antibiotic from Streptomyces tsukubaensis. In principle, it acts like ciclosporin. At the molecular level, however, its receptor is not cyclophilin but a so-called FK-binding protein. Tacrolimus is likewise used to prevent allograft rejection. Its epithelial penetrability is superior to that of ciclosporin, allowing topical application in atopic dermatitis. 

Macrolide antibiotic. From Streptomyces spinichromogenes var. kujmyceticus. Protein synth. inhibitor. Powder (Et20/ petrol). Sol. MeOH, Et20 poorly sol. El20, hexane. 

Maridomycins. The maridomycins are a new group of macrolide antibiotics from Streptomyces hygroscopicus and are designated maridomycins I— VI. The aglycones of the antibiotics have the general structure (108). ... 

Macrolide antibiotic from cultures of Streptomyces mycawfaciens. Midecamycin Aj, Aj and A4 exist also in small amounts in the complex beside main component Midecamycin. 

Kong F, Liu DQ, Nietsche J, Tischler M, Carter GT (1999) Colubricidin A, a Novel Macrolide Antibiotic from a Streptomyces sp. Tetrahedron Lett 40 9219... 

Quiros LM, Carbajo RJ, Brana AF et al (2000) Glycosylation of macrolide antibiotics. Purification and kinetic studies of a macrolide glycosyltransferase from Streptomyces antibioticus. J Biol Chem 275 11713-11720... 

JK Epp, MLB Huber, JR Turner, T Goodson, and BE Schoner. Production of a hybrid macrolide antibiotic in Streptomyces ambofaciens and Streptomyces lividans by introduction of a cloned carbomycin biosynthetic gene from Streptomyces ther-motolerans. Gene 85 293-301, 1989. 

Asolkar, R.N., Maskey, R.P., Helmke, E., and Laatsch, H. (2002) Chalcomycin B, a new macrolide antibiotic from the marine isolate Streptomyces sp. B7064./. Antibiot., 55, 893-898. 

P2j Z = 2 D = 1.17 R = 0.080 for 3,888 intensities. This is aconfigu-rational analysis of the macrolide antibiotic 23672RP from Streptomyces chryeus. All three sugar residues are pyranoid the conformation of the a-ketose is CX, with Q = 56 pm, 0 = 9° that of the / -D-mycinose (6-deoxy-2,3-di-0-methyl-D-allose) is 4Clt with Q = 59 pm, 0 = 6° and that of the / -L-mycarose (2,6-dideoxy-3-C-methyl-L-riho-hexose) is 1C4, with Q = 53 pm, 0= 177°. The O-5-C-l-O-l-C glycosidic torsion-angles are —71, —87, —83°. The atomic coordinates reported in the paper refer to the opposite enantiomer. 

Rochet and Lancelin50 reported revised 1H and 13C NMR assignments of the polyene antibiotic Filipin m (83). This macrolide which was isolated from Streptomyces filipinensis was reinvestigated in DMSO-dg solution using homonuclear and heteronuclear correlation spectroscopy. In addition to several corrections to previous 1H NMR... 

Macrolides, lincosamides and streptogramins are protein biosynthesis inhibitors that bind to 50S subunit of the ribosome and inhibit peptidyl tRNA translocation from the A-site to the P-site." Macrolides have a glycosylated 14-, 15- or 16-membered lactone ring structure and are produced by several species of Streptomyces. Lincosamide antibiotics were isolated initially from Streptomyces lincolnensis but later isolated from different species of Streptomcyces. Streptogramins were also isolated from Streptomycesgraminofaciens and subsequently from several different Streptomyces species. There are two structurally different streptogramins, A and B they are bacteriostatic individually and can be bactericidal when combined. 

Tacrolimus (previously known as FK506) is a macrolide antibiotic which is obtained from the fungus Streptomyces tsukubaensis. Tacrolimus binds in-tracellularly to the protein FKBP (FK binding protein) which is distinct from the protein that binds cyclosporine. However both drug-protein complexes associate in a similar way with calcineurin and inhibits its serine/threonine phosphatase activity, although the immunosuppressive potency of tacrolimus is approximately 100 fold higher than that of cyclosporine. 

Although it is not chemically related to cyclosporine, tacrolimus (6.7) has a similar mechanism of action. Tacrolimus is an immunosuppressant macrolide antibiotic derived from Streptomyces tsukubaenis. Like cyclosporine, tacrolimus inhibits the same cytoplasmic phosphatase, calcineurin, which catalyzes the activation of a T-cell-specific transcription factor (NF-AT) involved in the biosyntheses of interleukins such as IL-2. Sirolimus (6.8) is a natural product produced by Streptomyces hydroscopicus, it blocks the ability of T cells to respond to cytokines. 

Tacrolimus is a 23-membered lactone chain isolated in 1984 from Streptomyces tsukubaensis, although it was originally found in a soil fungus. It is a macrolide antibiotic, and its name is derived from Tsukuba macrolide immunosuppressant. ... 

Sirolimus is a macrolide antibiotic (macrocyclic lactone) first isolated from soil samples of Eastern Island as a product of the bacterium Streptomyces hygroscopicus and shares a lot of its structure with tacrolimus. 

This sugar is one of the two sugar units found in chalcomycins (155), 16-membered macrolide antibiotics,230 and in lankamycin (156), a 14-membered macrolide produced by Streptomyces sp. 231 The similar macrolide neutramycin (157) has been isolated with several analogues containing 4,6-dideoxy-D-xy/u-hexose (153) instead of chalcose (152) from cultures of S. luteoverticillatus.232... 

Jenkins G, Cundliffe E (1991) Cloning and characterization of two genes from Streptomyces lividans that confer inducible resistance to lincomycin and macrolide antibiotics. Gene 108 55-62... 

S. antibioticus produces another unusual macrolide antibiotic [45] called chlorothricin (57) containing, in addition to the aglycone (modified methylsalicylic acid), saccharides, dideoxyhexoses in the first place. Their biosynthesis was investigated by the incorporation of stable isotopes [45-47]. The compounds were only active in a synthetic medium and inactive in a complex one [48]. Compounds designated MC031-034 (58-61) are similar to chlorothricin mentioned above and were isolated from the cultivation broth of Streptomyces sp. collected in Japan. Another compound, 2-hydroxychlorothricin (62), with antitumor activity, was isolated [66] from Streptomyces K818. 

FK506 is the propriety name given to an immunosuppressant by a Japanese company. FK506 is a macrolide antibiotic, isolated from streptomyces tsukubaensis. It is a potent inhibitor of T cell activation, preventing allograft rejection. FK506 binds to FK-binding proteins, the FKBP s. 

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