References
- 1
Krow GR.
Org. React.
1993,
43:
251
- 2
Walsh CT.
Chen Y.-CJ.
Angew. Chem.
1988,
100:
342
- 3
Willetts A.
Trends Biotechnol.
1997,
15:
55
- 4
Roberts SM.
J. Mol. Catal. B: Enzym.
1998,
4:
111
- 5
Stewart JD.
Curr. Org. Chem.
1998,
2:
195
-
6a
Kelly DR.
Chim. Oggi
2000,
18:
33
-
6b
Kelly DR.
Chim. Oggi
2000,
18:
52
- 7
Bolm C.
Schlingloff G.
Weickhardt K.
Angew. Chem., Int. Ed. Engl.
1994,
33:
1848
- 8
Gusso A.
Baccin C.
Pinna F.
Strukul G.
Organometallics
1994,
13:
3442
- 9
Bolm C.
Schlingloff G.
J. Chem. Soc., Chem. Commun.
1995,
1247
- 10
Bolm C.
Schlingloff G.
Bienewald F.
J. Mol. Catal. A: Chemical
1997,
117:
347
- 11
Bolm C.
Luong TKK.
Schlingloff G.
Synlett
1998,
1151
- 12
Strukul G.
Varagnolo A.
Pinna F.
J. Mol. Catal. A: Chemical
1997,
117:
413
- 13
Bolm C.
Beckmann O.
Kühn T.
Palazzi C.
Adam W.
Rao PB.
Saha-Möller CR.
Tetrahedron: Asymmetry
2001,
12:
2441
- 14
Uchida T.
Katsuki T.
Tetrahedron Lett.
2001,
42:
6911
- 15
Vogel M.
Scharz-Linek U.
Bioorg. Chem.
1999,
102
- 16
Schwarz-Linek U.
Krödel A.
Ludwig F.-A.
Schulze A.
Rissom S.
Kragl U.
Tishkov VI.
Vogel M.
Synthesis
2001,
947
- 17
Donoghue NA.
Norris DB.
Trudgill PW.
Eur. J. Biochem.
1976,
63:
175
- 18
Kayser M.
Chen G.
Stewart J.
Synlett
1999,
153
- 19
Chen G.
Kayser MM.
Mihovilovic MD.
Mrstik ME.
Martinez CA.
Stewart JD.
New J. Chem.
1999,
23:
827
- 20
Griffin M.
Trudgill PW.
Biochem. J.
1972,
129:
595
- 21
Griffin M.
Trudgill PW.
Eur. J. Biochem.
1976,
63:
199
- 22
Trudgill PW.
Methods Enzymol.
1990,
188:
77
- 23
Bes MT.
Villa R.
Roberts SM.
Wan PWH.
Willetts AJ.
J. Mol. Catal. B: Enzym.
1996,
1:
127
- 24
Adger B.
Bes MT.
Grogan G.
McCague R.
Pedragosa-Moreau S.
Roberts SM.
Villa R.
Wan PWH.
Willetts AJ.
Bioorg. Med. Chem.
1997,
5:
253
- 26
Mihovilovic MD.
Chen G.
Wang S.
Kyte B.
Rochon F.
Kayser MM.
Stewart JD.
J. Org. Chem.
2001,
66:
733
- 27
Mihovilovic MD.
Müller B.
Kayser MM.
Stewart JD.
Fröhlich J.
Stanetty P.
Spreitzer H.
J. Mol. Catal. B: Enzym.
2001,
11:
349
- 28 For an alternative E. coli expression system for CHMO see: Doig SD.
O’Sullivan LM.
Patel S.
Ward JM.
Woodley JM.
Enzyme Microb. Technol.
2001,
28:
265
- 29 Application of the above system for whole-cell biotransformations: Simpson HD.
Alphand V.
Furstoss R.
J. Mol. Catal. B: Enzym.
2001,
16:
101
- 30
Riva R.
Banfi L.
Danieli B.
Guanti G.
Lesma G.
Palmisano G.
J. Chem. Soc., Chem. Commun.
1987,
299
- 31
Hieble JP.
Nichols AJ.
Langer SZ.
Ruffolo RR. In
Principles of Pharmacology
Munson PL.
Chapman and Hall;
New York:
1996.
p.135
- 32
Szántay C.
Honzy K.
Chem. Heterocycl. Compd.
1994,
25 (Suppl.):
161
- 33
Danieli B.
Lesma G.
Mauro M.
Palmisano G.
Passerella D.
Tetrahedron
1994,
50:
8837
- 34
Johns SR.
Lamberton JA.
Occolowitz JL.
J. Chem. Soc., Chem. Commun.
1967,
229
- 35
Krawczyk AR.
Jones JB.
J. Org. Chem.
1989,
54:
1795
- 36
Mundy BP.
Theodore JJ.
J. Am. Chem. Soc.
1980,
102:
2005
- 37
Aube J.
Gosh S.
Tanol M.
J. Am. Chem. Soc.
1994,
116:
9009
- 38
Barret AGM.
Boys ML.
Boehm TL.
J. Org. Chem.
1996,
61:
685
- 39
Bar R.
Trends Biotechnol.
1989,
7:
2
- 40
Miyafuji A.
Ito K.
Katsuki T.
Heterocycles
2000,
52:
261
25 Iwaki, H.; Hasegawa, Y.; Lau, P. C. K.; Wang, S.; Kayser, M. M. submitted to Appl. Environ. Microbiol.
41 Physical and spectroscopic data of lactones 2:
(4a
R
,8a
R
)-1,4,4a,5,8,8a-Hexahydro-3
H
-2-benzopyran-3-one(2a). Colorless oil; [α]D
20 = +24.5 (c 1.0, CHCl3); ee >99% (chiral phase GC); 1H NMR (200 MHz, CDCl3): δ = 1.80-2.13 (m, 2 H), 2.16-2.44 (m, 4 H), 2.50-2.60 (m, 2 H), 4.22-4.40 (m, 2 H), 5.67 (br s, 2 H); 13C NMR (50 MHz, CDCl3): δ = 24.0 (t), 28.4 (t), 28.5 (d), 29.6 (d), 33.7 (t), 72.1 (t), 124.1 (d), 124.6 (d), 170.6 (s).
(4a
R
,8a
R
)
-
Octahydro-3
H
-2-benzopyran-3-one(2b). Colorless oil; [α]D
20 = +39.1 (c 1.0, CHCl3); ee = 99% (chiral phase GC); 1H NMR (200 MHz, CDCl3): δ = 1.22-1.63 (m, 8 H), 1.83-2.01 (m, 1 H), 2.05-2.25 (m, 1 H), 2.40-2.55 (m, 2 H), 4.25 (d, 2 H, J = 8 Hz); 13C NMR (50 MHz, CDCl3): δ = 21.5 (t), 23.3 (t), 24.6 (t), 28.6 (t), 31.0 (d), 32.7 (d), 32.8 (t), 72.4 (t), 171.1 (s).