Synthesis and applications of silicon-containing α-amino acids

被引:149
作者
Mortensen, Matthew [1 ]
Husmann, Ralph [1 ]
Veri, Elisabetta [1 ]
Bolm, Carsten [1 ]
机构
[1] Univ Aachen, Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
关键词
BUILDING FUNCTIONALIZED PEPTIDOMIMETICS; UND SILAZAN-CARBONSAUREESTER; N-ACYLIMINIUM IONS; ASYMMETRIC-SYNTHESIS; C/SI/GE BIOISOSTERISM; ENZYMATIC PREPARATION; HYDROXYACETIC ACIDS; PEPTIDES; SILAPROLINE; PROLINE;
D O I
10.1039/b816769a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Amino acids serve not only as monomers for proteins and enzymes but also as important players in signal transduction pathways. They belong to the abundant feedstock of the pharmaceutical, food science and agrochemical industries, and some are used as catalysts or ligand components. In recent years, non-proteogenic amino acids have taken on important roles. This tutorial review summarises the progress in the development of strategies to construct silicon-containing alpha-amino acid frameworks and the studies concerned with their structure and activity. It shall be of interest for the synthesis and biosciences communities.
引用
收藏
页码:1002 / 1010
页数:9
相关论文
共 52 条
  • [1] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
  • [2] BIRKOFER L, 1958, LIEBIGS ANN CHEM, V612, P22
  • [3] NEUE SILICIUM-ORGANISCHE VERBINDUNGEN - SILICOAMINOSAUREN UND SILAZAN-CARBONSAUREESTER
    BIRKOFER, L
    RITTER, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1956, 68 (14) : 461 - 462
  • [4] Synthesis of novel silylated 1,2,4-triazin-5-ones
    Bolm, C
    Kasyan, A
    Saladin, S
    [J]. TETRAHEDRON LETTERS, 2005, 46 (23) : 4049 - 4051
  • [5] Enantiopure α-silyl-substituted α-hydroxyacetic acids using O-H insertion methodology and boron-based asymmetric reductions
    Bolm, C
    Saladin, S
    Classen, A
    Kasyan, A
    Veri, E
    Raabe, G
    [J]. SYNLETT, 2005, (03) : 461 - 464
  • [6] Intermolecular rhodium(II)-catalyzed reactions with silicon-substituted carbonyl ylides
    Bolm, C
    Saladin, S
    Kasyan, A
    [J]. ORGANIC LETTERS, 2002, 4 (26) : 4631 - 4633
  • [7] Synthesis and use of α-silyl-substituted α-hydroxyacetic acids
    Bolm, C
    Kasyan, A
    Heider, P
    Saladin, S
    Drauz, K
    Günther, K
    Wagner, C
    [J]. ORGANIC LETTERS, 2002, 4 (13) : 2265 - 2267
  • [8] Bolm C, 2000, ANGEW CHEM INT EDIT, V39, P2288, DOI 10.1002/1521-3773(20000703)39:13<2288::AID-ANIE2288>3.0.CO
  • [9] 2-Y
  • [10] Hydantoin-hydrolysing enzymes for the enantioselective production of amino acids: new insights and applications
    Burton, SG
    Dorrington, RA
    [J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (18) : 2737 - 2741