Pseudomonic Acids
Title: Pseudomonic Acids
Literature References: A group of antibacterial antibiotics produced by Pseudomonas fluorescens NCIB 10586 that have unusual structural features. Four members of the group are known: pseudomonic acid A, the major component; pseudomonic acid B, the 3,4,5-trihydroxy analog of A (also referred to as pseudomonic acid I); pseudomonic acid D, the 4-nonenoic acid analog of A; and pseudomonic acid C, in which the epoxide oxygen is replaced by a double bond. Isoln and characterization of A and B: A. T. Fuller et al., Nature 234, 416 (1971); K. D. Barrow, G. Mellows, DE 2227739; eidem, US 3977943 (1973, 1976 both to Beecham). Structure of B: E. B. Chain, G. Mellows, J. Chem. Soc. Perkin Trans. 1 1977, 318. Prepn of C: N. H. Rogers, P. J. O'Hanlon, EP 3069; eidem, US 4205002 (1979, 1980 both to Beecham). Isoln, structure, configuration of C: J. P. Clayton et al., Tetrahedron Lett. 21, 881 (1980). Total syntheses of naturally occurring (+)-form of C: A. P. Kozikowski et al., J. Am. Chem. Soc. 102, 6577 (1980); in high yield: C. Mckay et al., Chem. Commun. 2000, 1109; of racemic A or C: B. B. Snider, G. B. Phillips, J. Am. Chem. Soc. 104, 1113 (1982); B. B. Snider et al., J. Org. Chem. 48, 3003 (1983). Prepn of D: P. J. O¢Hanlon, EP 68680 (1983 to Beecham), C.A. 98, 159135t (1983); P. J. O¢Hanlon et al., J. Chem. Soc. Perkin Trans. 1 1983, 2655. Antimycoplasmal activity in vitro: R. M. Banks et al., J. Antibiot. 41, 609 (1988).
Properties: Isolated as a mixture of sodium salts. Can be stored at 0° for several months with no activity loss. Stable within pH 4-9 at 37° for 24 hrs. Hemolytic; inactivated by serum at conc >50%.
 
Derivative Type: Pseudomonic Acid A see Mupirocin
 
Derivative Type: Pseudomonic Acid C
CAS Registry Number: 71980-98-8
CAS Name: (2E)-5,9-Anhydro-2,3,4,8-tetradeoxy-8-[(2E,4R,5S)-5-hydroxy-4-methyl-2-hexenyl]-3-methyl-L-talo-non-2-enonic acid 8-carboxyoctyl ester
Molecular Formula: C26H44O8
Molecular Weight: 484.62
Percent Composition: C 64.44%, H 9.15%, O 26.41%
Properties: [a]D25 +7.64° (c = 0.78 in chloroform). uv max (ethanol): 222 nm (e 14100).
Optical Rotation: [a]D25 +7.64° (c = 0.78 in chloroform)
Absorption maximum: uv max (ethanol): 222 nm (e 14100)
 
Derivative Type: Pseudomonic Acid D
CAS Registry Number: 85248-93-7
CAS Name: (2E)-5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]oxiranyl]methyl]-L-talo-non-2-enoic acid (5E)-8-carboxy-5-octenyl ester
Molecular Formula: C26H42O9
Molecular Weight: 498.61
Percent Composition: C 62.63%, H 8.49%, O 28.88%
Properties: Oil. uv max (ethanol): 220 nm (e 15499).
Absorption maximum: uv max (ethanol): 220 nm (e 15499)

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