Practical synthesis of fully-substituted peptide thiazoles

被引:11
作者
Buchanan, JL [1 ]
Mani, UN [1 ]
Plake, HR [1 ]
Holt, DA [1 ]
机构
[1] ARIAD Pharmaceut Inc, Cambridge, MA 02139 USA
关键词
thiazoles; amido-ketones; amino acids and derivatives; Grignard reactions reagents;
D O I
10.1016/S0040-4039(99)00659-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of optically active 2,4,5-substituted 1,3-thiazoles (peptide thiazoles) is described. Both the chirality and the set of side chain functionality in this fully-substituted scaffold are derived from a combination of two amino acids and one organometallic reagent. Preliminary results, with two specific examples, highlight the potential of this strategy for the preparation of a diverse set of building blocks, (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3985 / 3988
页数:4
相关论文
共 32 条
  • [1] Conformational control by thiazole and oxazoline rings in cyclic octapeptides of marine origin. Novel macrocyclic chair and boat conformations
    Abbenante, G
    Fairlie, DP
    Gahan, LR
    Hanson, GR
    Pierens, GK
    vandenBrenk, AL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (43) : 10384 - 10388
  • [2] REINVESTIGATION OF A MODIFIED HANTZSCH THIAZOLE SYNTHESIS
    AGUILAR, E
    MEYERS, AI
    [J]. TETRAHEDRON LETTERS, 1994, 35 (16) : 2473 - 2476
  • [3] Synthesis of functionalised oxazoles and bis-oxazoles
    Bagley, MC
    Buck, RT
    Hind, SL
    Moody, CJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03): : 591 - 600
  • [4] Kinetics and regioselectivity of peptide-to-heterocycle conversions by microcin B17 synthetase
    Belshaw, PJ
    Roy, RS
    Kelleher, NL
    Walsh, CT
    [J]. CHEMISTRY & BIOLOGY, 1998, 5 (07): : 373 - 384
  • [5] THE CHIRAL SYNTHESIS OF THIAZOLE AMINO-ACID ENANTIOMERS
    BREDENKAMP, MW
    HOLZAPFEL, CW
    VANZYL, WJ
    [J]. SYNTHETIC COMMUNICATIONS, 1990, 20 (15) : 2235 - 2249
  • [6] The chemistry of pseudomonic acid .15. Synthesis and antibacterial activity of a series of 5-alkyl, 5-alkenyl, and 5-heterosubstituted oxazoles
    Brown, P
    Davies, DT
    OHanlon, PJ
    Wilson, JM
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (02) : 446 - 457
  • [7] BUCHANAN JW, UNPUB
  • [8] TOTAL SYNTHESIS OF IONOPHORE ANTIBIOTIC X-14547A (INDANOMYCIN)
    BURKE, SD
    PISCOPIO, AD
    KORT, ME
    MATULENKO, MA
    PARKER, MH
    ARMISTEAD, DM
    SHANKARAN, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02) : 332 - 347
  • [9] Biochemistry - Harnessing the biosynthetic code: Combinations, permutations, and mutations
    Cane, DE
    Walsh, CT
    Khosla, C
    [J]. SCIENCE, 1998, 282 (5386) : 63 - 68
  • [10] Design, synthesis, activity, and structure of a novel class of matrix metalloproteinase inhibitors containing a heterocyclic P-2'-P-3' amide bond isostere
    Chen, JJ
    Zhang, YP
    Hammond, S
    Dewdney, N
    Ho, T
    Lin, XH
    Browner, MF
    Castelhano, AL
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (13) : 1601 - 1606