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Volumn 38, Issue 3, 2010, Pages 829-837

(S)-α-methyl,α-amino acids: A new stereocontrolled synthesis

Author keywords

Methyl amino acids; Asymmetric synthesis; Diketopiperazine derivatives

Indexed keywords

1,4 N,N (1 PHENYLETHYL)PIPERAZINE 2,5 DIONE; 2 BENZYLALANINE; 2 BUTYLYLALANINE; 2 ETHYLALANINE; 2 PROPYLALANINE; 2,5 PIPERAZINEDIONE; ALPHA AMINO ACID; ALPHA METHYL ALPHA AMINO ACID; PIPERAZINE DERIVATIVE; PIPERAZINEDIONE; UNCLASSIFIED DRUG;

EID: 77951666710     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-009-0289-9     Document Type: Article
Times cited : (10)

References (26)
  • 1
    • 33748832564 scopus 로고    scopus 로고
    • Structures of peptaibol antibiotics hypomurocin A and B from the ascomycetous fungus Hypocrea muroiana Hino et Katsumoto
    • Becker D, Kiess M, Bruckner H (1997) Structures of peptaibol antibiotics hypomurocin A and B from the ascomycetous fungus Hypocrea muroiana Hino et Katsumoto. Liebigs Ann Recueil 767 (Pubitemid 127789434)
    • (1997) Liebigs Annales , Issue.4 , pp. 767-772
    • Becker, D.1    Kiess, M.2    Bruckner, H.3
  • 2
    • 0032483491 scopus 로고    scopus 로고
    • Stereoselective synthesis of uncommon α,α'-dialkyl-α- aminoacids. Part 1
    • DOI 10.1016/S0957-4166(98)00272-9, PII S0957416698002729
    • A Carloni G Porzi S Sandri 1998 Stereoselective synthesis of uncommon α,α'-dialkyl-α-amino acids. Part 1 Tetrahedron Asymmetry 9 2987 10.1016/S0957-4166(98)00272-9 10.1016/S0957-4166(98)00272-9 1:CAS:528:DyaK1cXntVSnt7s%3D (Pubitemid 28475186)
    • (1998) Tetrahedron Asymmetry , vol.9 , Issue.17 , pp. 2987-2998
    • Carloni, A.1    Porzi, G.2    Sandri, S.3
  • 3
    • 0032561221 scopus 로고    scopus 로고
    • Stereoselective synthesis of quaternary α-amino acids. Part 1: Acyclic compounds
    • DOI 10.1016/S0957-4166(98)00391-7, PII S0957416698003917
    • C Cativiela M Diaz-De-Villegas 1998 Stereoselective synthesis of quaternary α-amino acids. Part 1: acyclic compounds Tetrahedron Asymmetry 9 3517 10.1016/S0957-4166(98)00391-7 10.1016/S0957-4166(98)00391-7 1:CAS:528:DyaK1cXnvVCjtLo%3D (Pubitemid 28529720)
    • (1998) Tetrahedron Asymmetry , vol.9 , Issue.20 , pp. 3517-3599
    • Cativiela, C.1    Diaz-De-Villegas, M.D.2
  • 6
    • 0034670565 scopus 로고    scopus 로고
    • Applications of the sulfinimine-mediated asymmetric strecker synthesis to the synthesis of α-alkyl α-amino acids
    • 10.1021/jo001179z 10.1021/jo001179z 1:CAS:528:DC%2BD3cXotVyhtrs%3D 11112592
    • FA Davis S Lee H Zhang DL Fanelli 2000 Applications of the sulfinimine-mediated asymmetric strecker synthesis to the synthesis of α-alkyl α-amino acids J Org Chem 65 8704 10.1021/jo001179z 10.1021/jo001179z 1:CAS:528:DC%2BD3cXotVyhtrs%3D 11112592
    • (2000) J Org Chem , vol.65 , pp. 8704
    • Davis, F.A.1    Lee, S.2    Zhang, H.3    Fanelli, D.L.4
  • 7
    • 0037150553 scopus 로고    scopus 로고
    • Stereoselective synthesis of bis(α-amino acid) derivatives isosteric of cysteine. Part 4
    • DOI 10.1016/S0957-4166(02)00262-8, PII S0957416602002628
    • F Ferioli F Piccinelli G Porzi S Sandri 2002 Stereoselective synthesis of bis(α-amino acid) derivatives isosteric with cysteine. Part 4 Tetrahedron Asymmetry 13 1181 10.1016/S0957-4166(02)00262-8 10.1016/S0957-4166(02)00262-8 1:CAS:528:DC%2BD38XlsVelt7o%3D (Pubitemid 34786575)
    • (2002) Tetrahedron Asymmetry , vol.13 , Issue.11 , pp. 1181-1187
    • Ferioli, F.1    Piccinelli, F.2    Porzi, G.3    Sandri, S.4
  • 8
    • 0033555780 scopus 로고    scopus 로고
    • Towards control of χ-space: Conformationally constrained analogues of Phe, Tyr, Trp and His
    • DOI 10.1016/S0040-4020(98)00942-9, PII S0040402098009429
    • SE Gibson N Guillo MJ Tozer 1999 Towards control of x-space: conformationally constrained analogues of Phe, Tyr, Trp and His Tetrahedron 55 585 10.1016/S0040-4020(98)00942-9 10.1016/S0040-4020(98)00942-9 1:CAS:528:DyaK1MXpvVGnsw%3D%3D (Pubitemid 29023309)
    • (1999) Tetrahedron , vol.55 , Issue.3 , pp. 585-615
    • Gibson, S.E.1    Guillo, N.2    Tozer, M.J.3
  • 9
    • 84985527649 scopus 로고
    • Asymmetric synthesis of amines by carbon-carbon coupling in the α-position to nitrogen
    • 10.1002/anie.198007251 10.1002/anie.198007251
    • M Kolb J Barth 1980 Asymmetric synthesis of amines by carbon-carbon coupling in the α-position to nitrogen Angew Chem Int Ed Engl 19 725 10.1002/anie.198007251 10.1002/anie.198007251
    • (1980) Angew Chem Int Ed Engl , vol.19 , pp. 725
    • Kolb, M.1    Barth, J.2
  • 10
    • 0006050830 scopus 로고
    • Synthesis of optically pure alpha-alkylated alpha-amino acids and a single-step method for enantiomeric excess determination
    • 10.1021/jo00243a049 10.1021/jo00243a049 1:CAS:528:DyaL1cXhs1Kjsbs%3D
    • WH Kruizinga J Bolster RM Kellogg J Kamphuis WHJ Boesten EM Meijer J Schoemaker 1988 Synthesis of optically pure alpha-alkylated alpha-amino acids and a single-step method for enantiomeric excess determination Org Chem 53 1826 10.1021/jo00243a049 10.1021/jo00243a049 1:CAS:528:DyaL1cXhs1Kjsbs%3D
    • (1988) Org Chem , vol.53 , pp. 1826
    • Kruizinga, W.H.1    Bolster, J.2    Kellogg, R.M.3    Kamphuis, J.4    Boesten, W.H.J.5    Meijer, E.M.6    Schoemaker, J.7
  • 12
    • 0037844251 scopus 로고    scopus 로고
    • Asymmetric synthesis of alpha-methyl alpha-amino acids through diastereoselective alkylation under mild reaction conditions of an iminic alanine template with a 1,2,3,6-tetrahydro-2-pyrazinone structure
    • 10.1002/1099-0690(200008)2000:15<2809::AIDEJOC2809>3.0.CO;2-X
    • Najera C, Abellan T, Sansano JM (2000) Asymmetric synthesis of alpha-methyl alpha-amino acids through diastereoselective alkylation under mild reaction conditions of an iminic alanine template with a 1,2,3,6-tetrahydro-2- pyrazinone structure. Eur J Org Chem 2809. doi: 10.1002/1099-0690(200008)2000: 15<2809::AIDEJOC2809>3.0.CO;2-X
    • (2000) Eur J Org Chem , pp. 2809
    • Najera, C.1    Abellan, T.2    Sansano, J.M.3
  • 13
    • 0027068120 scopus 로고
    • Diastereoselective alkylation of (3S)- and (3R)-3-methylpiperazine-2,5- dione derivatives. A convenient approach to both (S)- and (R)-alanine
    • DOI 10.1021/jo00050a030
    • M Orena G Porzi S Sandri 1992 Diastereoselective alkylation of (3S)- and (3R)-3-methylpiperazine-2,5-dione derivatives. A convenient approach to both (S)- and (R)-alanine J Org Chem 57 6532 10.1021/jo00050a030 10.1021/jo00050a030 1:CAS:528:DyaK38XmtlCnur4%3D (Pubitemid 23017303)
    • (1992) Journal of Organic Chemistry , vol.57 , Issue.24 , pp. 6532-6536
    • Orena, M.1    Porzi, G.2    Sandri, S.3
  • 14
    • 0002110393 scopus 로고
    • (3R)-Methylpiperazine-2 and (3S)-methylpiperazine-2,5-dione derivatives as useful intermediates in the enantioselective synthesis of alpha-amino esters
    • Orena M, Porzi G, Sandri S (1993) (3R)-Methylpiperazine-2 and (3S)-methylpiperazine-2,5-dione derivatives as useful intermediates in the enantioselective synthesis of alpha-amino esters. J Chem Res Synop 318
    • (1993) J Chem Res Synop , vol.318
    • Orena, M.1    Porzi, G.2    Sandri, S.3
  • 15
    • 0034680460 scopus 로고    scopus 로고
    • Stereoselective synthesis of α,α′-diamino-dicarboxylic acids. Part 2
    • DOI 10.1016/S0957-4166(00)00450-X, PII S095741660000450X
    • F Paradisi G Porzi S Rinaldi S Sandri 2000 Stereoselective synthesis of α, α'-diamino-dicarboxylic acids part 2 Tetrahedron Asymmetry 11 4617 10.1016/S0957-4166(00)00450-X 10.1016/S0957-4166(00)00450-X 1:CAS:528:DC%2BD3MXjt1emsg%3D%3D (Pubitemid 32121711)
    • (2000) Tetrahedron Asymmetry , vol.11 , Issue.22 , pp. 4617-4622
    • Paradisi, F.1    Porzi, G.2    Rinaldi, S.3    Sandri, S.4
  • 16
    • 0034616096 scopus 로고    scopus 로고
    • A simple asymmetric synthesis of (+)- and (-)-2,6-diaminopimelic acids
    • DOI 10.1016/S0957-4166(00)00050-1, PII S0957416600000501
    • F Paradisi G Porzi S Rinaldi S Sandri 2000 A simple asymmetric synthesis of (+)- and (-)-2,6-diaminopimelic acids Tetrahedron Asymmetry 11 1259 10.1016/S0957-4166(00)00050-1 10.1016/S0957-4166(00)00050-1 1:CAS:528: DC%2BD3cXjt1Cju7c%3D (Pubitemid 30256050)
    • (2000) Tetrahedron Asymmetry , vol.11 , Issue.6 , pp. 1259-1262
    • Paradisi, F.1    Porzi, G.2    Rinaldi, S.3    Sandri, S.4
  • 17
    • 0037023454 scopus 로고    scopus 로고
    • Enantioselective synthesis of 2,6-diaminopimelic acid derivatives. Part 3
    • DOI 10.1016/S0957-4166(02)00126-X, PII S095741660200126X
    • F Paradisi F Piccinelli G Porzi S Sandri 2002 Enantioselective synthesis of 2,6-diaminopimelic acid derivatives. Part 3 Tetrahedron Asymmetry 13 497 10.1016/S0957-4166(02)00126-X 10.1016/S0957-4166(02)00126-X 1:CAS:528: DC%2BD38XjtVGjtL4%3D (Pubitemid 34327763)
    • (2002) Tetrahedron Asymmetry , vol.13 , Issue.5 , pp. 497-502
    • Paradisi, F.1    Piccinelli, F.2    Porzi, G.3    Sandri, S.4
  • 18
    • 0037423132 scopus 로고    scopus 로고
    • Stereocontrolled synthesis of enantiomerically pure unsaturated analogues of 2,6-DAP. Part 5
    • DOI 10.1016/S0957-4166(02)00834-0, PII S0957416602008340
    • F Piccinelli G Porzi M Sandri S Sandri 2003 Stereocontrolled synthesis of enantiomerically pure unsaturated analogues of 2,6-DAP. Part 5 Tetrahedron Asymmetry 14 393 10.1016/S0957-4166(02)00834-0 10.1016/S0957-4166(02)00834-0 1:CAS:528:DC%2BD3sXptFaisA%3D%3D (Pubitemid 36160598)
    • (2003) Tetrahedron Asymmetry , vol.14 , Issue.3 , pp. 393-398
    • Piccinelli, F.1    Porzi, G.2    Sandri, M.3    Sandri, S.4
  • 19
    • 0028350483 scopus 로고
    • Synthesis of (3R,6R)- and (3S,6S)-3,6-dialkylpiperazin-2,5-dione derivatives as useful intermediates to both (R) and (S) α-aminoacids
    • DOI 10.1016/S0957-4166(00)86217-5
    • G Porzi S Sandri 1994 Synthesis of (3R,6R)- and (3S,6S)-3,6- dialkylpiperazin-2,5-dione derivatives as useful intermediates to both (R) and (S) α-amino acids Tetrahedron Asymmetry 5 453 10.1016/S0957-4166(00)86217- 5 10.1016/S0957-4166(00)86217-5 1:CAS:528:DyaK2cXmsFKhtbY%3D (Pubitemid 24117575)
    • (1994) Tetrahedron Asymmetry , vol.5 , Issue.3 , pp. 453-464
    • Porzi, G.1    Sandri, S.2
  • 20
    • 0032476152 scopus 로고    scopus 로고
    • A new stereoselective synthesis of sterically constrained uncommon α,α'-dialkylated α-amino acids. Part 2
    • DOI 10.1016/S0957-4166(98)00360-7, PII S0957416698003607
    • G Porzi S Sandri 1998 A new stereoselective synthesis of sterically constrained uncommon alpha,alpha-dialkylated alpha-amino acids. Part 2 Tetrahedron Asymmetry 9 3411 10.1016/S0957-4166(98)00360-7 1:CAS:528: DyaK1cXnslejtLg%3D and references contained therein (Pubitemid 28529552)
    • (1998) Tetrahedron Asymmetry , vol.9 , Issue.19 , pp. 3411-3420
    • Porzi, G.1    Sandri, S.2
  • 21
    • 33846597094 scopus 로고    scopus 로고
    • Recent approaches towards the asymmetric synthesis of α,α- disubstituted α-amino acids
    • DOI 10.1039/b611091f
    • H Vogt S Brase 2007 Study of inclusive strange-baryon production and search for pentaquarks in two-photon collisions at LEP Org Biomol Chem 5 406 10.1039/b611091f 1:CAS:528:DC%2BD2sXoslShsA%3D%3D 17252120 and references contained therein (Pubitemid 46170762)
    • (2007) Organic and Biomolecular Chemistry , vol.5 , Issue.3 , pp. 406-430
    • Vogt, H.1    Brase, S.2
  • 22
    • 0000003184 scopus 로고
    • 2-(Hydroxymethyl) aspartic acid: Synthesis, crystal structure, and reaction with a transaminase
    • 10.1021/ja00543a058 10.1021/ja00543a058
    • JJ Walsh DE Metzler D Powel RA Jacobson 1980 2-(Hydroxymethyl) aspartic acid: synthesis, crystal structure, and reaction with a transaminase J Am Chem Soc 102 7138 10.1021/ja00543a058 10.1021/ja00543a058
    • (1980) J Am Chem Soc , vol.102 , pp. 7138
    • Walsh, J.J.1    Metzler, D.E.2    Powel, D.3    Jacobson, R.A.4
  • 23
    • 0030955088 scopus 로고    scopus 로고
    • New strategies to α-alkylated α-amino acids
    • T Wirth 1997 New strategies to α-alkylated α-amino acids Angew Chem Int Ed Engl 36 225 10.1002/anie.199702251 10.1002/anie.199702251 1:CAS:528:DyaK2sXhsVWrt7s%3D (Pubitemid 27133908)
    • (1997) Angewandte Chemie - International Edition in English , vol.36 , Issue.3 , pp. 225-227
    • Wirth, T.1
  • 24
    • 33744905212 scopus 로고    scopus 로고
    • Asymmetric synthesis of α,α-disubstituted α-amino acids by diastereoselective alkylation of camphor-based tricyclic iminolactone
    • DOI 10.1021/jo052435g
    • Peng-Fei Xu Shou Li Ta-Jumg Lu Chen-Chang Wu Botao Fan Georgia Golfin 2005 Asymmetric synthesis of α,α-disubstituted α-amino acids by diastereoselective alkylation of camphor-based tricyclic iminolactone J Org Chem 71 4364 10.1021/jo052435g 10.1021/jo052435g (Pubitemid 43849537)
    • (2006) Journal of Organic Chemistry , vol.71 , Issue.12 , pp. 4364-4373
    • Xu, P.-F.1    Li, S.2    Lu, T.-J.3    Wu, C.-C.4    Fan, B.5    Golfis, G.6
  • 26
    • 0031468922 scopus 로고    scopus 로고
    • MS-681a, b, c and d, new inhibitors of myosin light chain kinase from Myrothecium sp. KY6568. I. Characterization of producing strain and production, isolation and biological activities
    • S Yano Y Nakanishi Y Ikuina K Ando M Yoshida Y Saitoh Y Matsuda C Bando 1997 MS-681a, b, c and d, new inhibitors of myosin light chain kinase from Myrothecium sp. KY6568-I. Characterization of producing strain and production, isolation and biological activities J Antibiot 50 992 1:CAS:528: DyaK1cXit1KnsQ%3D%3D 9510904 (Pubitemid 28045930)
    • (1997) Journal of Antibiotics , vol.50 , Issue.12 , pp. 992-997
    • Yano, H.1    Nakanishi, S.2    Ikuina, Y.3    Ando, K.4    Yoshida, M.5    Saitoh, Y.6    Matsuda, Y.7


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