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. 2010 Apr 15;87(1):41–52. doi: 10.1007/s00253-010-2530-6

Table 1.

Potential applications for selected R-HAs as synthons

R-HAs Potential synthon for Reference
(R)-3-hydroxyundec-10-enoate Inhibitor of cholesterol synthesis, effects 3-hydroxy-3-methyl-glutaryl (HMG) CoA synthetase Dirat et al. (1998)
Precursor of L-659,699 (inhibitor of cholesterol biosynthesis) Chiang et al. (1989)
(R)-3-hydroxy-undecanoate Depsipeptides (antibiotic/antifungal) Nihei et al. (2005); Wohlrab et al. (2007)
(−)-tetrahydrolipstatin (anti-obesity drug) Pons and Kocienski (1989); Sarabia and Chammaa (2005)
Lipid A mimic (immunobiological) Martin et al. (2006)
Stevastelins B and B3 Sarabia and Chammaa (2005)
Sulfobacin A Gupta et al. (2004); Irako and Shioiri (1998); Labeeuw et al. (2004)
Globomycin (antibiotic, signal peptidase II inhibitor) Kiho et al. (2003a); Kiho et al. (2003b, 2004)
Pseudomycin Rodriguez et al. (2001)
Topostins B567 and D654 Irako and Shioiri (1998)
(R)-3-hydroxy-nonanoate Globomycin analogs (antibiotic) Kiho et al. (2004)
(R)-2-benzylcyclohexanone (precursor of natural products) Katoh et al. (1994)
(R)-3-hydroxyoctanoate Simvastatin (antihypercholesterolemic, inhibitor of HMG-CoA reductase Lee and Lee (2004); Morgan and Burk (2005)
Viscosin Hiramoto (1971)
(R)-3-hydroxyhept-6-enoate Potent HMG CoA reductase inhibitor FR901512 Inoue and Nakada (2007)
Rosuvastatin calcium, a HMG CoA reductase inhibitors Zlicar (2007)
α,β-disubstituted β-lactones Wu and Sun (2005)
Sphingofungin D (antifungal) Mori and Otaka (1994); Vanmiddlesworth et al. (1992)
Sphingofungin F (antifungal) Kobayashi et al. (1997)
Precursor of β-lactams for synthesis of carbacephems (class of antibiotics) Crocker and Miller (1995)
Ebelactone A and B (β-lactone enzyme inhibitor) Paterson and Hulme (1995)
Bicycloheptenones Marotta et al. (1994b)
Cyclosporine A derivatives (immunosuppressive) Aebi et al. (1990); Colucci et al. (1990); Lynch et al. (1987); Rich et al. (1989); Schmidt and Siegel (1987); Schreiber et al. (1988)
(S)-citronellol Hirama et al. (1985)
(R)-3-hydroxyheptanoate Anachelin (siderophore of Anabaena cylindrica) Ito et al. (2004)
Pravastatin (atherosclerosis/hypercholesteremia agent) Keri et al. (2007)
(R)-3-hydroxyhexanoate Analogs of laulimalide (paclitaxel like antimicrotubule agent) Faveau et al. (2006)