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Volumn 65, Issue 9, 2001, Pages 1977-1980

Enzyme-assisted Preparation of D-tert.-Leucine

Author keywords

Alcalase ; Bacillus licheniformis; D tert. leucine; Enzymatic hydrolysis; Protease

Indexed keywords

BACILLUS LICHENIFORMIS;

EID: 0035460619     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.65.1977     Document Type: Article
Times cited : (25)

References (26)
  • 2
    • 0000772371 scopus 로고
    • Syntheses of 3,3-dimethyl-2-hydroxybutyric acid and tertiary leucine and their optical resolutions
    • Tanabe, T., Yajima, S., and Imaida, M., Syntheses of 3,3-dimethyl-2-hydroxybutyric acid and tertiary leucine and their optical resolutions. Bull. Chem. Soc. Jpn., 41, 2178-2179 (1968).
    • (1968) Bull. Chem. Soc. Jpn. , vol.41 , pp. 2178-2179
    • Tanabe, T.1    Yajima, S.2    Imaida, M.3
  • 3
    • 0011361133 scopus 로고
    • Untersuchungen über das konfigurative Verhalten von Pseudoleucin bei der Waldenschen Umkehrung und über die Abspaltung von Halogen durch verdünnte Alkali aus raumisomeren α-Brom-β-trimethyl-propionyl-aminosäuren
    • Abderhalden, E., Faust, W., and Haase, E., Untersuchungen über das konfigurative Verhalten von Pseudoleucin bei der Waldenschen Umkehrung und über die Abspaltung von Halogen durch verdünnte Alkali aus raumisomeren α-Brom-β-trimethyl-propionyl-aminosäuren. Z. physiol. Chem., 228, 187-197 (1934).
    • (1934) Z. Physiol. Chem. , vol.228 , pp. 187-197
    • Abderhalden, E.1    Faust, W.2    Haase, E.3
  • 4
    • 0000469739 scopus 로고
    • Simple optical resolution of terleucine
    • Viret, J., Patzelt, H., and Collet, A., Simple optical resolution of terleucine. Tetrahedron Lett., 27, 5865-5868 (1986).
    • (1986) Tetrahedron Lett. , vol.27 , pp. 5865-5868
    • Viret, J.1    Patzelt, H.2    Collet, A.3
  • 5
    • 0001168462 scopus 로고
    • Über optisch aktives tert.-Leucin und Pinacolylamin
    • Pracejus, H., and Winter, S., Über optisch aktives tert.-Leucin und Pinacolylamin. Chem. Ber., 97, 3173-3182 (1964).
    • (1964) Chem. Ber. , vol.97 , pp. 3173-3182
    • Pracejus, H.1    Winter, S.2
  • 6
    • 0000147841 scopus 로고
    • Studies on unusual amino acids and their peptides X. the convenient synthesis of t-leucine and the optical resolution of the N-benzoyloxycarbonyl derivative
    • Miyazawa, T., Takashima, K,. Mitsuda, Y., Yamada, T., Kuwata, S., and Watanabe, H., Studies on unusual amino acids and their peptides X. The convenient synthesis of t-leucine and the optical resolution of the N-benzoyloxycarbonyl derivative. Bull. Chem. Soc. Jpn., 52, 1539-1540 (1979).
    • (1979) Bull. Chem. Soc. Jpn. , vol.52 , pp. 1539-1540
    • Miyazawa, T.1    Takashima, K.2    Mitsuda, Y.3    Yamada, T.4    Kuwata, S.5    Watanabe, H.6
  • 7
    • 0016650748 scopus 로고
    • The circular dichroism of N-thiobenzoyl-L-α-amino-acids. Part VI. Assessment of the resolutin of amino-acids as their N-thiobenzoyl derivatives
    • Barrett, G. C., and Cousins, P. R., The circular dichroism of N-thiobenzoyl-L-α-amino-acids. Part VI. Assessment of the resolutin of amino-acids as their N-thiobenzoyl derivatives. J. Chem. Soc. Perkin Trans. I., 1975, 2313-2315.
    • (1975) J. Chem. Soc. Perkin Trans. I , pp. 2313-2315
    • Barrett, G.C.1    Cousins, P.R.2
  • 8
    • 84984174739 scopus 로고
    • Umwandlung von racem. Tert.-Leucin in das L-Enantiomere
    • Steglich, W., and Weygand, F., Umwandlung von racem. Tert.-Leucin in das L-Enantiomere. Chem. Ber., 104, 687-690 (1971).
    • (1971) Chem. Ber. , vol.104 , pp. 687-690
    • Steglich, W.1    Weygand, F.2
  • 9
    • 33845375340 scopus 로고
    • Stereoselective amination of chiral enolates. A new approach to the asymetric synthesis of α-hydrazino and α-amino acid derivatives
    • Evans, D., Britton, T., Dorow, R., and Dellaria, J., Stereoselective amination of chiral enolates. A new approach to the asymetric synthesis of α-hydrazino and α-amino acid derivatives. J. Am. Chem. Soc., 108, 6395-6397 (1986).
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 6395-6397
    • Evans, D.1    Britton, T.2    Dorow, R.3    Dellaria, J.4
  • 10
    • 38849119887 scopus 로고
    • Carbohydrates as chiral templates: Diastereoselective Ugi synthesis of (S)-amino acids using O-acylated D-arabino-pyranosylamine as the auxiliary
    • Kunz, H., Pfrengle, W., and Sager, W., Carbohydrates as chiral templates: Diastereoselective Ugi synthesis of (S)-amino acids using O-acylated D-arabino-pyranosylamine as the auxiliary. Tetrahedron Lett., 30, 4109-4110 (1989).
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4109-4110
    • Kunz, H.1    Pfrengle, W.2    Sager, W.3
  • 11
    • 84989540865 scopus 로고
    • A General, Catalytic, and enantioselective synthesis of α-amino acids
    • Corey, E., and Link, J., A General, Catalytic, and enantioselective synthesis of α-amino acids. J. Am. Chem. Soc., 114, 1906-1908 (1992).
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 1906-1908
    • Corey, E.1    Link, J.2
  • 12
    • 0000297984 scopus 로고
    • An efficent and practical synthesis of L-α-amino acids using (R)-phenylglycinol as a chiral auxiliary
    • Inaba, T., Kozono, I., Kujita, M., and Ogura, K., An efficent and practical synthesis of L-α-amino acids using (R)-phenylglycinol as a chiral auxiliary. Bull. Chem. Soc. Jpn., 65, 2359-2365 (1992).
    • (1992) Bull. Chem. Soc. Jpn. , vol.65 , pp. 2359-2365
    • Inaba, T.1    Kozono, I.2    Kujita, M.3    Ogura, K.4
  • 15
    • 0028891799 scopus 로고
    • Synthesis of homochiral L-(S)-tert.-leucine via a lipase catalysed dynamic resolution process
    • Turner, N., Wintermann, R., McCague, R., Parratt, J., and Taylor, J., Synthesis of homochiral L-(S)-tert.-leucine via a lipase catalysed dynamic resolution process. Tetrahedron. Lett., 36, 1113-1116 (1995).
    • (1995) Tetrahedron. Lett. , vol.36 , pp. 1113-1116
    • Turner, N.1    Wintermann, R.2    McCague, R.3    Parratt, J.4    Taylor, J.5
  • 16
    • 0002036742 scopus 로고
    • Continuous cofactor regeneration-utilization of polymer bound NAD(H) for the production of optically active acids
    • Wandrey, C., and Bossow, B., Continuous cofactor regeneration-utilization of polymer bound NAD(H) for the production of optically active acids. Biotechnol. Bioind., 3, 8-13 (1986).
    • (1986) Biotechnol. Bioind. , vol.3 , pp. 8-13
    • Wandrey, C.1    Bossow, B.2
  • 18
    • 84907037937 scopus 로고
    • Some new developments in reductive amination with cofactor regeneration
    • Bommarius, A., Drauz, K., Hummel, W., Kula, M-R., and Wandrey, C., Some new developments in reductive amination with cofactor regeneration. Biocatalysis, 10, 37-47 (1994).
    • (1994) Biocatalysis , vol.10 , pp. 37-47
    • Bommarius, A.1    Drauz, K.2    Hummel, W.3    Kula, M.-R.4    Wandrey, C.5
  • 19
    • 85005697480 scopus 로고
    • Dehydrogenases for the synthesis of chiral compounds
    • Hummel, W., and Kula, M.-R., Dehydrogenases for the synthesis of chiral compounds. Eur. J. Biochem., 184, 1-13 (1989).
    • (1989) Eur. J. Biochem. , vol.184 , pp. 1-13
    • Hummel, W.1    Kula, M.-R.2
  • 20
    • 84989579302 scopus 로고
    • Synthesis of (R)-tert.-leucinol by classical resolution of the racemic mixture
    • Drauz, K., Jahn, W., and Schwarm, M., Synthesis of (R)-tert.-leucinol by classical resolution of the racemic mixture. Chem. Eur. J., 1, 538-540 (1995).
    • (1995) Chem. Eur. J. , vol.1 , pp. 538-540
    • Drauz, K.1    Jahn, W.2    Schwarm, M.3
  • 21
    • 0347304022 scopus 로고    scopus 로고
    • note
    • Lipase CE (Amano, 4% rel. activ.), Bioprase SP4 (Nagase, 13% rel. activ.), Prozyme 6 (Amano, 15% rel. activ.), Protease N (Amano, 60% rel. activ.), Alcalase (Novo, 100% rel. activ.).
  • 22
    • 0346673474 scopus 로고    scopus 로고
    • Higher pH values are not recommended in order to avoid chemical hydrolysis of the substrate
    • Higher pH values are not recommended in order to avoid chemical hydrolysis of the substrate.
  • 23
    • 0347304023 scopus 로고
    • Ph.D. Thesis, BUGH-Wuppertal
    • Laumen, K., Ph.D. Thesis, BUGH-Wuppertal, 1987
    • (1987)
    • Laumen, K.1
  • 24
    • 0347304018 scopus 로고    scopus 로고
    • Novo Nordisk, Alcalase 2.5L, Type DX, PMN04666, 2.67 AU/g proteolytic activity
    • Novo Nordisk, Alcalase 2.5L, Type DX, PMN04666, 2.67 AU/g proteolytic activity.
  • 25
    • 0347304021 scopus 로고    scopus 로고
    • note
    • For the isolation of (S)-2, the aqueous phase from dichloromethane extraction was brought to pH 1 by addling a concentrated HCl solution. The formed precipitate was removed by centrifugation and washed with water. (S)-2 was obtained in 90% yield with an enantiomeric purity of 95.6% (HPLC), but was not further processed.
  • 26
    • 0000930508 scopus 로고
    • Synthese des Pseudoleucins
    • Knoop, F., and Landmann, G., Synthese des Pseudoleucins, Z. physiol. Chem., 89, 157-159, (1914).
    • (1914) Z. Physiol. Chem. , vol.89 , pp. 157-159
    • Knoop, F.1    Landmann, G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.