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Volumn 118, Issue 26, 1996, Pages 6295-6296

Use of deuterium kinetic isotope effects to probe the cryptoregiochemistry of Δ9 desaturation

Author keywords

[No Author keywords available]

Indexed keywords

ACYL COENZYME A DESATURASE; FATTY ACID DERIVATIVE;

EID: 0030018325     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953262n     Document Type: Article
Times cited : (77)

References (26)
  • 1
    • 0001819717 scopus 로고
    • D. E., Vance, J. E., Eds.; The Benjamin Cummings Publishing Co. Ltd.: Menlo Park, CA
    • Cook, H. In Biochemistry of Lipids and Membranes Vance, D. E., Vance, J. E., Eds.; The Benjamin Cummings Publishing Co. Ltd.: Menlo Park, CA, 1985; pp 191-203.
    • (1985) Biochemistry of Lipids and Membranes Vance , pp. 191-203
    • Cook, H.1
  • 8
    • 8944252231 scopus 로고    scopus 로고
    • note
    • 11 (not shown) are involved in these reactions cannot be excluded at the present time.
  • 9
    • 0029197421 scopus 로고
    • Very recent results from the Newcomb laboratory have suggested that this species is not a true intermediate but, at least in the case of certain cyclopropylcarbinyl radicals, behaves as "a component of a reacting ensemble" with a very short lifetime of ca. 70 fs: Newcomb, M.; Letadicbiadetti, F. H.; Chestney, D. L.; Roberts, E. S.; Hollenberg, P. F. J. Am. Chem. Soc. 1995, 117, 12085.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 12085
    • Newcomb, M.1    Letadicbiadetti, F.H.2    Chestney, D.L.3    Roberts, E.S.4    Hollenberg, P.F.5
  • 17
    • 8944228821 scopus 로고    scopus 로고
    • note
    • 4
  • 18
    • 0001166830 scopus 로고
    • Buist, P. H.; Dallmann, H. G.; Rymerson, R. R.; Seigel, P. M.; Skala, P. Tetrahedron Lett. 1988, 29, 435. Our whole cell system allows us to use thiastearate methyl esters which are presumably converted intracellularly to the corresponding CoA thioesters prior to desaturation. The thiaoleate products can then be isolated by a cell hydrolysis/methylation sequence. The use of S. cerevisiae under conditions of adequate glucose supply prevents extensive metabolism of the thiastearate substrates and/or the thiaoleate products which in turn might lead to nondesaturase-related isotopic fractionation.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 435
    • Buist, P.H.1    Dallmann, H.G.2    Rymerson, R.R.3    Seigel, P.M.4    Skala, P.5
  • 19
    • 8944228367 scopus 로고    scopus 로고
    • note
    • 3.
  • 20
    • 0000385707 scopus 로고
    • A small proportion (<10%) of the observed isotope effect may be due to an α-secondary isotope effect. Cf.: Jones, J. P.; Trager, W. F. J. Am. Chem. Soc. 1987, 109, 2171.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2171
    • Jones, J.P.1    Trager, W.F.2
  • 21
    • 0000385707 scopus 로고
    • The magnitude of the primary deuterium isotope effect at C-9 must be regarded as a lower limit for the "intrinsic" kinetic isotope effect since our value is derived via an intermolecular competition experiment and is therefore subject to partial masking by other enzymic steps. Large "intrinsic" primary deuterium isotope effects are not uncommon for biological hydrocarbon activations thought to involve iron-oxo species. Cf. ref 16.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2171
    • Jones, J.P.1    Trager, W.F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.