TY - JOUR
T1 - Stereo- and regioselective hydroxylation of α-ionone by Streptomyces strains
AU - Lutz-Wahl, Sabine
AU - Fischer, Peter
AU - Schmidt-Dannert, Claudia
AU - Wohlleben, Wolfgang
AU - Hauer, Bernhard
AU - Schmid, Rolf D.
PY - 1998/10
Y1 - 1998/10
N2 - A total of 215 Streptomyces strains were screened for their capacity to regio- and stereoselectively hydroxylate β- and/or α-ionone to the respective 3-hydroxy derivatives. With β-ionone as the substrate, 15 strains showed little conversion to 4-hydroxy- and none showed conversion to the 3- hydroxy product as desired. Among these 15 Streptomyces strains, S. fradiae Tu 27, S. arenae Tu 495, S. griseus ATCC 13273, S. violaceoniger Tu 38, and S. antibioticus Tu 4 and Tu 46 converted α-ionone to 3-hydroxy-α-ionone with significantly higher hydroxylation activity compared to that of β- ionone. Hydroxylation of racemic α-ionone [(6R)-(-)/(6S)-(+)] resulted in the exclusive formation of only the two enantiomers (3R,6R)- and (3S,6S)- hydroxy-α-ionone. Thus, the enzymatic hydroxylation of α-ionone by the Streptomyces strains tested proceeds with both high regio- and stereoselectivity.
AB - A total of 215 Streptomyces strains were screened for their capacity to regio- and stereoselectively hydroxylate β- and/or α-ionone to the respective 3-hydroxy derivatives. With β-ionone as the substrate, 15 strains showed little conversion to 4-hydroxy- and none showed conversion to the 3- hydroxy product as desired. Among these 15 Streptomyces strains, S. fradiae Tu 27, S. arenae Tu 495, S. griseus ATCC 13273, S. violaceoniger Tu 38, and S. antibioticus Tu 4 and Tu 46 converted α-ionone to 3-hydroxy-α-ionone with significantly higher hydroxylation activity compared to that of β- ionone. Hydroxylation of racemic α-ionone [(6R)-(-)/(6S)-(+)] resulted in the exclusive formation of only the two enantiomers (3R,6R)- and (3S,6S)- hydroxy-α-ionone. Thus, the enzymatic hydroxylation of α-ionone by the Streptomyces strains tested proceeds with both high regio- and stereoselectivity.
UR - http://www.scopus.com/inward/record.url?scp=0031692755&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0031692755&partnerID=8YFLogxK
U2 - 10.1128/aem.64.10.3878-3881.1998
DO - 10.1128/aem.64.10.3878-3881.1998
M3 - Article
C2 - 9758813
AN - SCOPUS:0031692755
SN - 0099-2240
VL - 64
SP - 3878
EP - 3881
JO - Applied and environmental microbiology
JF - Applied and environmental microbiology
IS - 10
ER -