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Volumn 8, Issue 1, 2006, Pages 58-65

Microwave-assisted parallel synthesis of a 14-helical β-peptide library

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDE; PEPTIDE LIBRARY;

EID: 31544463846     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0501099     Document Type: Article
Times cited : (53)

References (58)
  • 10
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    • Rapid parallel synthesis utilizing microwave irradiation
    • Sucholeiki, I., Ed.; Marcel Dekker: New York
    • (b) Glass, B. M.; Combs, A. P. Rapid Parallel Synthesis Utilizing Microwave Irradiation. In High-Throughput Synthesis; Sucholeiki, I., Ed.; Marcel Dekker: New York, 2001; pp 123-128.
    • (2001) High-Throughput Synthesis , pp. 123-128
    • Glass, B.M.1    Combs, A.P.2
  • 11
    • 1642579961 scopus 로고    scopus 로고
    • Microwave-assisted combinatorial chemistry
    • Loupy, A. Ed.; Wiley-VCH: Weinheim
    • (c) Kappe, C. O.; Stadler, A. Microwave-Assisted Combinatorial Chemistry. In Microwaves in Organic Synthesis; Loupy, A. Ed.; Wiley-VCH: Weinheim, 2002; pp 405-433.
    • (2002) Microwaves in Organic Synthesis , pp. 405-433
    • Kappe, C.O.1    Stadler, A.2
  • 12
    • 20044376318 scopus 로고    scopus 로고
    • For selected examples employing the CombiCHEM module for the Milestone MicroSYNTH Labstation, see: (a) Alcázar, J. J. Comb. Chem. 2005, 7, 353.
    • (2005) J. Comb. Chem. , vol.7 , pp. 353
    • Alcázar, J.1
  • 46
    • 31544462268 scopus 로고    scopus 로고
    • note
    • CEM Discover
  • 47
    • 31544475624 scopus 로고    scopus 로고
    • note
    • CEM MARS
  • 49
    • 14844346398 scopus 로고    scopus 로고
    • By raising the temperature to 80°C for coupling and 90 °C for Fmoc-deprotection, we obtained β-peptide 1 in 89% purity using the multimode microwave reactor, similar to our best results with the monomode reactor (ref 2). The higher temperatures for synthesis in the multimode instrument were surprising, because earlier attempts to increase reaction temperature in the monomode instrument (60 °C set temperature for coupling) led to the formation of a side-product via premature Fmoc-deprotection and addition of a second monomer unit during the double-coupling of the N-terminal ACHC to form β-peptide 3. Although higher temperatures may be beneficial for the difficult reaction steps, we found through subsequent work that the polypropylene filter plates were not stable to these conditions. The discrepancy in optimized temperatures between the two different reactors may be explained by the following factors. In the monomode reactor, the combination of continuous cooling of the sample (Leadbeater, N. E.; Pillsbury, S. J.; Shanahan, E.; Williams, V. A. Tetrahedron 2005, 61, 3565), the experimental set up (ref 2), and the built-in IR temperature sensor, which measures the external temperature of the glass reaction vessel (ref 23), result in an observed temperature that is much lower than the internal temperature of the reaction mixture measured more accurately with the fiber-optic probe of the multimode instrument.
    • (2005) Tetrahedron , vol.61 , pp. 3565
    • Leadbeater, N.E.1    Pillsbury, S.J.2    Shanahan, E.3    Williams, V.A.4
  • 56
    • 31544455465 scopus 로고    scopus 로고
    • note
    • Reaction vessels were 4.0-mL polypropylene solid-phase extraction tubes; turntable available from CEM.
  • 58
    • 31544474542 scopus 로고    scopus 로고
    • note
    • This is an average of 95% for each of the 10 reaction steps.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.