Synthesis of Rhodotorulic Acid

Isowa, Yoshikazu; Takashima, Tsuyoshi; Ohmori, Muneki; Kurita, Hideaki; Sato, Masanari; Mori, Katsuharu

doi:10.1246/bcsj.45.1467

Cited by 22 publications

(6 citation statements)

References 5 publications

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“…Subsequent removal of the tosyl groups followed by N-acetylation and hydrogenolytic removal of the benzyl protecting groups and addition of ferric ion gave ferrichrome (Scheme 18) . 93 Keller-Schierlein's group later published a synthesis of enantioferrichrome (Scheme 19). 78 In this case, the cyclohexapeptide (D-Orn)3-Gly3 (94) was first prepared by conventional methods.…”

Section: Synthetic Design and Synthesis Of Siderophore Componentsmentioning

confidence: 99%

Syntheses and therapeutic potential of hydroxamic acid based siderophores and analogs

Miller¹

1989

Chem. Rev.

305

180

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Section: Synthetic Design and Synthesis Of Siderophore Componentsmentioning

confidence: 99%

Syntheses and therapeutic potential of hydroxamic acid based siderophores and analogs

Miller¹

1989

Chem. Rev.

305

180

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“…Isowa et al have synthesized protected N5hydroxyornithine from achiral building blocks and enzymatically resolved the racemic product into its enantiomers. These served as precursors for the synthesis of DD-RA and LL-RA (16). The chromic complexes of the naturally occurring LL-RA, and by analogy the predominant configuration of the ferric complex in aqueous solution, has been shown to be A (7).…”

mentioning

confidence: 99%

Iron transport in Streptomyces pilosus mediated by ferrichrome siderophores, rhodotorulic acid, and enantio-rhodotorulic acid

Ga¹,

Matzanke²,

Raymond³

1984

J Bacteriol

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Streptomyces pilosus is one of several microbes which produce ferrioxamine siderophores. In the accompanying paper (G. Muller and K. Raymond, J. Bacteriol. 160:304-312), the mechanism of iron uptake mediated by the endogenous ferrioxamines B, DI, D2, and E was examined. Here we report iron transport behavior in S. pilosus as mediated by the exogenous siderophores ferrichrome, ferrichrysin, rhodotorulic acid (RA), and synthetic enantio-RA. In each case iron acquisition depended on metabolic energy and had uptake rates comparable to that of [55Fe]ferrioxamine B. However, the synthetic ferric enantio-RA (which has the same preferred chirality at the metal center as fet-richrome) was twice as effective in supplying iron as was the natural ferric RA complex, suggesting that stereospecific recognition at the metal center is involved in the transport process. Iron uptake mediated by ferrichrome and ferric enantio-RA was strongly inhibited by kinetically inert chromic complexes of desferrioxamine B. These inhibition experiments indicate that iron from these exogenous siderophores Is transported by the same uptake system as ferrioxamine B. Since the ligands have no structural similarity to ferrioxamine B except for the presence of three hydoxamate groups, we conclude that only the hydroxamate iron center and its direct surroundings are important for recognition and uptake. This hypothesis is supported by the fact that ferrichrome A and ferrirubin, which are both substituted at the hydroxamate carbonyl groups, were not (or were poorly) effective in supplying iron to S. pilosus.

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“…Synthesis of l-Hydroxy-3(S)-amino-2-piperidone. The synthesis of HAP has been reported previously (Emery, 1966, Isowa et al, 1972. A convenient method, corresponding to the synthesis of 3-acetylamino-l-hydroxy-2-piperidone (Atkin, 1970), is reported here.…”

mentioning

confidence: 99%

“…The resulting HAP was purified by ion exchange (see above) and crystallized in 70-75% yield as the hydrochloride salt from ethanol, mp 205-208°( lit. 211-212°, Emery (1966); 208-215°, Isowa et al (1972)).…”

mentioning

confidence: 99%

Hydroxamic acid present in Rhodotorula pilimanae cultures grown at low pH and its metabolic relation to rhodotorulic acid

Akers¹,

Neilands²

1973

Biochemistry

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Rhodotorula pilimanae CBS 4479, when grown at pH 2.8 in iron-limited media, produced rhodotorulic acid and a second hydroxamic acid which was characterized as 1hydroxy-3(S)-amino-2-piperidone (HAP). The latter, which was not converted to rhodotorulic acid, was shown to arise from cyclization of -yV-hydroxyornithine. The addition of iron to growing cultures effected a parallel depression of have previously reviewed the features of rhodotorulic acid which render it the substance of choice for biosynthetic studies in the siderochrome (iron transport compound) series (Akers et a!., 1972). Rhodotorulic acid was thought to arise from --hydroxyornithine (OHOrn)1; however, due to the instability of OHOrn at pH values above the hydroxylamine pKlx of 5.5 we were reluctant to examine this compound as a precursor. In an attempt to overcome this problem we adapted Rhodotorula pilimanae to grow at pH 2.8. A hydroxamic acid produced at this pH differed from rhodotorulic acid in that it was retained by a cation exchange resin.This paper deals with the purification, characterization by comparison with synthetic material, and origin of 1-hydroxy-3(S)-amino-2-piperidone (HAP). The results indicate that at low pH OHOrn, a direct precursor of rhodotorulic acid, is diverted into the medium where it is cyclized nonenzymatically to HAP. Materials and MethodsR. pilimanae cultures adapted to low pH were maintained as liquid cultures on low pH ASKP medium (see below). Crystalline rhodotorulic acid was obtained from low-iron cultures of R. pilimanae (Atkin and Neilands, 1968). OHOrn was from HC1 hydrolysates of rhodotorulic acid (Atkin and Neilands, 1968).5-lV-Acetyl-5-/V-hydroxyornithine (AcOHOrn) was synthesized from OHOrn (Akers et al., 1972).Medium. R. pilimanae was cultured for 10-14 days at 30°o n a rotary shaker in the ASKP medium previously described (Akers et a!., 1972). The pH was adjusted to 2.8 • 0.1 using concentrated H3P04. Iron (as ferric ammonium sulfate)was not added unless specifically stated.Hydroxamates were determined spectrophotometrically (Atkin and Neilands, 1968). A tetrazolium spray was used for the detection of hydroxylamines (Snow, 1954

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Synthesis of Rhodotorulic Acid

Cited by 22 publications

References 5 publications

Syntheses and therapeutic potential of hydroxamic acid based siderophores and analogs

Syntheses and therapeutic potential of hydroxamic acid based siderophores and analogs

Iron transport in Streptomyces pilosus mediated by ferrichrome siderophores, rhodotorulic acid, and enantio-rhodotorulic acid

Hydroxamic acid present in Rhodotorula pilimanae cultures grown at low pH and its metabolic relation to rhodotorulic acid

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