Reaction SMILES: P(OC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1O)(OP(OP(O)(O)=O)(O)=O)(=O)O.[Mg+2].[Cl-].[Cl-].CC([C@@H](O)C(NCCC(NCCS)=O)=O)(COP(OP(OC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1OP(O)(O)=O)(O)=O)(O)=O)C.O[C@H](CCCCC)CC([O-])=O.S(=O)(=O)(O)O.[OH:99][C@H:100]([CH2:152][CH2:153][C:154]1C=CC=[CH:156][CH:155]=1)[CH2:101][C:102]([S:104][CH2:105][CH2:106][NH:107][C:108](=[O:151])[CH2:109][CH2:110][NH:111][C:112](=[O:150])[C@H:113]([OH:149])[C:114]([CH3:148])([CH3:147])[CH2:115][O:116][P:117]([OH:146])(=[O:145])[O:118][P:119]([OH:144])(=[O:143])[O:120][CH2:121][C@H:122]1[O:126][C@@H:125]([N:127]2[C:136]3[N:135]=[CH:134][N:133]=[C:131]([NH2:132])[C:130]=3[N:129]=[CH:128]2)[C@H:124]([OH:137])[C@@H:123]1[O:138][P:139]([OH:142])([OH:141])=[O:140])=[O:103].O[C@H](CCC1C=CC(F)=CC=1)CC(SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1OP(O)(O)=O)=O>>[OH:99][C@H:100]([CH2:152][CH2:153][CH2:154][CH2:155][CH3:156])[CH2:101][C:102]([S:104][CH2:105][CH2:106][NH:107][C:108](=[O:151])[CH2:109][CH2:110][NH:111][C:112](=[O:150])[C@H:113]([OH:149])[C:114]([CH3:148])([CH3:147])[CH2:115][O:116][P:117]([OH:146])(=[O:145])[O:118][P:119]([OH:144])(=[O:143])[O:120][CH2:121][C@H:122]1[O:126][C@@H:125]([N:127]2[C:136]3[N:135]=[CH:134][N:133]=[C:131]([NH2:132])[C:130]=3[N:129]=[CH:128]2)[C@H:124]([OH:137])[C@@H:123]1[O:138][P:139]([OH:142])([OH:141])=[O:140])=[O:103]
Reactant: CC(C)(COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@H](O)CCc1ccccc1
Agent: CC(C)(COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O)[C@@H](O)C(=O)NCCC(=O)NCCS
Agent: CC(C)(COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@H](O)CCc1ccc(F)cc1
Agent: CCCCC[C@@H](O)CC(=O)[O-]
Product: CCCCC[C@@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O

Procedure:
(R)-3-hydroxyoctanoyl-CoA was synthesized in accordance with the following procedure, based on the method of Rehm BHA, Kruger N, Steinbuchel A (1998) Journal of Biological Chemistry 273 pp 24044–24051, with the method slightly modified. Acyl-CoA synthetase (manufactured by Sigma Co., Ltd.) was dissolved in a tris hydrochloric buffer solution (50 mM, pH 7.5) containing 2 mM ATP, 5 mM MgCl2, 2 mM CoA and 2 mM (R)-3-hydroxyoctanoate so that the concentration was 0.1 milliunit per microliter. The solution was stored in a warm bath at 37° C., and was sampled at appropriate times to analyze the progress of the reaction by HPLC. Sulfuric acid was added in the sampled reaction solution to make a concentration 0.02 N to stop the enzyme reaction, and thereafter (R)-3-hydroxyoctanoate being an unreacted substrate was extracted with n-heptane and removed. For the analysis by HPLC, using a RP18 column (nucleosil C18, 7 μm, Knauser), elution was conducted with the linear concentration gradient of acetonitrile using a 25 mM phosphate buffer solution (pH 5.3) as a mobile phase, and absorption spectra of 200 to 500 nm were monitored by a diode array detector, thereby detecting a thioester compound produced through the enzyme reaction. In a similar way, (R)-3-hydroxy-5-phenylvaleryl CoA, and (R)-3-hydroxy-5-(4-fluorophenyl)valeryl CoA were prepared.