Chloroperoxidase-mediated asymmetric epoxidation. Synthesis of (R)- dimethyl 2-methylaziridine-1,2-dicarboxylate - A potential α-methylamino acid synthon

Tetrahedron Asymmetry

Volumn 8, Issue 21, 1997, Pages 3547-3550

  Lakner, Frederick J ^a   Hager, Lowell P ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; AZIRIDINE DERIVATIVE; CHLORIDE PEROXIDASE; CHROMIC ACID; DICARBOXYLIC ACID DERIVATIVE; PYRIDINIUM DERIVATIVE; TITANIUM;

ARTICLE; ENZYME SUBSTRATE; EPOXIDATION; PRIORITY JOURNAL; PROTEIN DEGRADATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0031566702     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00467-9     Document Type: Article

References (29)

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17. 6. Of the protecting groups for methallylamine that were investigated - formyl, acetyl, trifluoroacetyl, t-butoxycarbonyl, and methoxycarbonyl - the latter was determined to be the most efficiently epoxidized by CPO.
18. 7. Obtained from Chirazyme Laboratories, 2004 S. Wright St., Urbana, IL 61801, USA.
19. 3: 145.07389. Found: 145.07385.
20. 9. Since the fungus cements itself to the sides of the roller flasks and secretes CPO, the supernatant is virtually cell-free and possesses good CPO activity.
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23. 2O) gave excellent yields of N-substituted epoxy carbamates.
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26. 3: C, 39.68%; H, 6.66%; Cl, 19.52%; N, 7.71%. Found: C, 39.68%; H, 6.85%; Cl, 19.27%; N, 8.11%.
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28. 4: C, 36.84%; H, 5.15%; Cl, 18.12%; N, 7.16%. Found: C, 36.74%; H, 5.18%; 18.21%; N, 7.45%.
29. 4: C, 48.55%; H, 6.40%; N, 8.09%. Found: C, 48.30%; H, 6.44%; N, 8.16%.