Perimycin

Perimycin
Names
IUPAC name
(1R,3S,5S,7R,9R,13R,17R,18S,19E,21E,23Z,25Z,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,7,9,13,37-heptahydroxy-17-[(2S)-5-hydroxy-7-[4-(methylamino)phenyl]-7-oxoheptan-2-yl]-18,36-dimethyl-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-11,15-dione
Other names
4ʼ-Amino-3ʼ-deamino-18-decarboxy-40-demethyl-4ʼ-deoxy-3,7-dideoxo-3,3ʼ,7-trihydroxy-N47,18,dimethyl-5-oxocandicidin-D-cyclic-15,19-hemiacetal
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C59H88N2O17/c1-36-18-16-14-12-10-8-6-7-9-11-13-15-17-19-49(76-58-56(73)55(72)54(60)39(4)75-58)33-52-38(3)51(70)35-59(74,78-52)34-48(68)30-46(66)28-44(64)26-43(63)27-45(65)29-47(67)32-53(71)77-57(36)37(2)20-25-42(62)31-50(69)40-21-23-41(61-5)24-22-40/h6-19,21-24,36-39,42-44,46-49,51-52,54-58,61-64,66-68,70,72-74H,20,25-35,60H2,1-5H3/b7-6-,10-8-,11-9+,14-12+,15-13+,18-16+,19-17+/t36-,37-,38+,39+,42?,43+,44-,46-,47+,48-,49-,51-,52-,54+,55-,56-,57-,58-,59+/m0/s1
    Key: SIJFZOSSGXKJCI-FTNWOYNKSA-N
SMILES
  • O=C1C[C@@H](O)CC(OC([C@@H](C)CCC(O)CC(C4=CC=C(NC)C=C4)=O)([H])[C@@H](C)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](O[C@@]3([H])[C@@H](O)[C@@H](O)[C@H](N)[C@@H](C)O3)C[C@]([C@H](C)[C@@H](O)C2)([H])O[C@@]2(O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C1)=O
Properties
Chemical formula
 C59H88N2O17
Molar mass 1097.33 g/mol
Appearance Amorphous, golden-yellow solid
Melting point Indefinite
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Perimycin, also known as aminomycin and fungimycin, is polyene antibiotic produced by Streptomyces coelicolor var. aminophilus.[1][2][3][4] The compound exhibits antifungal properties.

Composition

Perimycin is produced naturally as a mixture of three types: A, B and C, with type A being the major component. All types consist of a polyketide core with a perosamine sugar moiety. The variations occur at the end of the core opposite the perosamine moiety. Perimycin A has an aromatic group in this position, whereas the identities of the analogous groups in the other perimycin types are currently undetermined.

Usage

Polyene antibiotics in general are often toxic to humans and have poor bioavailability. Thus, with the notable exception of amphotericin B, they are often not used clinically. Perimycin has been shown to be an effective antifungal compound, but is not widely used in clinical settings.[5]

References

  1. ↑ Hamilton-Miller JM (June 1973). "Chemistry and biology of the polyene macrolide antibiotics". Bacteriological Reviews. 37 (2): 166–96. doi:10.1128/br.37.2.166-196.1973. PMC 413810. PMID 4578757.
  2. ↑ Liu CM, McDaniel LE, Schaffner CP (March 1972). "Fungimycin, biogenesis of its aromatic moiety". The Journal of Antibiotics. 25 (3): 187–8. doi:10.7164/antibiotics.25.187. PMID 5034814.
  3. ↑ Lee CH, Schaffner CP (May 1969). "Perimycin. The structure of some degradation products". Tetrahedron. 25 (10): 2229–32. doi:10.1016/S0040-4020(01)82770-8. PMID 5788396.
  4. ↑ Pawlak J, Sowiński P, Borowski E, Gariboldi P (September 1995). "Stereostructure of perimycin A". The Journal of Antibiotics. 48 (9): 1034–8. doi:10.7164/antibiotics.48.1034. PMID 7592049.
  5. ↑ Elmer, Y. Tu; Charlotte E. Joslina; Lisa M. Nijmc; Robert S. Federd; Sandeep Jaina; Megan E. Shoffe (July 2009). "Polymicrobial Keratitis: Acanthamoeba and Infectious Crystalline Keratopathy". American Journal of Ophthalmology. 148 (1): 13–19.e2. doi:10.1016/j.ajo.2009.01.020. PMC 2830559. PMID 19327742.


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