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Volumn 68, Issue 25, 2003, Pages 9541-9553

Synthesis of 3-Aminolactams as X-Gly Constrained Pseudodipeptides and Conformational Study of a Trp-Gly Surrogate

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CONFORMATIONS; NUCLEAR MAGNETIC RESONANCE; POLYPEPTIDES; SYNTHESIS (CHEMICAL);

EID: 0344666683     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035151+     Document Type: Article
Times cited : (31)

References (67)
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    • For biological relevance of Trp see: http: //www.acdlabs.com/publish/tryptophan/.
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    • This reagent is compatible with the presence of other functional groups, see: (c) Hamada, Y.; Shiori, T. J. Org. Chem. 1986, 51, 5489-5490.
    • (1986) J. Org. Chem. , vol.51 , pp. 5489-5490
    • Hamada, Y.1    Shiori, T.2
  • 20
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    • note
    • When N-deprotection was performed with TFA at 0 °C piperidone 6 was obtained in 63% yield accompanied by 3-(benzyloxycarbonyl)piperidin-2-one (13%) as a byproduct, see Experimental Section.
  • 21
    • 0003979828 scopus 로고    scopus 로고
    • Academic Press: London, UK
    • (a) Sundberg, R. J. Indoles; Academic Press: London, UK, 1996; pp 105-107.
    • (1996) Indoles , pp. 105-107
    • Sundberg, R.J.1
  • 22
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    • Properties and Reactions of Indoles
    • John Wiley and Sons: New York
    • (b) Remers, W. A. Properties and Reactions of Indoles. In Heterocyclic Compounds. Indoles. Part I; John Wiley and Sons: New York, 1972; pp 100-105.
    • (1972) Heterocyclic Compounds. Indoles. Part I , pp. 100-105
    • Remers, W.A.1
  • 30
    • 0003148146 scopus 로고
    • Stabilized Nucleophiles with Electron Deficient Alkenes and Alkynes
    • Pergamon Press: Oxford, UK
    • (b) Jung, M. E. Stabilized Nucleophiles with Electron Deficient Alkenes and Alkynes. In Comprehensive Organic Synthesis; Pergamon Press: Oxford, UK, 1991; Vol. 4, pp 1-67.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1-67
    • Jung, M.E.1
  • 31
    • 0002701930 scopus 로고
    • Conjugate Additions of Reactive Carbanions to Activated Alkenes and Alkynes
    • Pergamon Press: Oxford, UK
    • (c) Lee, V. J. Conjugate Additions of Reactive Carbanions to Activated Alkenes and Alkynes. In Comprehensive Organic Synthesis; Pergamon Press: Oxford, UK, 1991; Vol. 4, pp 70-137.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 70-137
    • Lee, V.J.1
  • 38
    • 2642676149 scopus 로고
    • To obtain the carbamate with the amino group protected with Fmoc, (9-fluorenyl)methanol was used, instead of BnOH, but the reaction failed, see: Evans, D. A.; Black, C. J. Am. Chem. Soc. 1993, 115, 4497-4513.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4497-4513
    • Evans, D.A.1    Black, C.2
  • 40
    • 0344990548 scopus 로고    scopus 로고
    • note
    • 2 in AcOEt at room temperature.
  • 52
    • 0021779081 scopus 로고
    • The major β-turns are classified according to the torsion angles of the second (φ1, ψ1: φ1 = -60 ± 30° and ψ1 = 120 ± 30°) and third amino acids (φ2, ψ2: φ2 = 80 ± 30° and ψ2 = 0 ± 45°), see: (a) Rose, G. D.; Gierash, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1-109.
    • (1985) Adv. Protein Chem. , vol.37 , pp. 1-109
    • Rose, G.D.1    Gierash, L.M.2    Smith, J.A.3
  • 55
    • 0344127948 scopus 로고    scopus 로고
    • note
    • The main features characterizing a classical γ-turn are the torsion angles of the second amino acid (φ2, ψ2: φ2 = 70°/85° and ψ2 = -60°/-70°) and the distance between the carbonyl carbon atom of the second amino acid (i+1) and the nitrogen atom of the amino group of the third residue (i+3) with a preferential value of 3 Å, see ref 27a.
  • 59
    • 0020163940 scopus 로고
    • The temperature coefficients in DMSO, according to Kessler criteria, suggested that in diastereomer I protons NHa and NHc (|Δδ/ΔT| < 3 ppb/K) were intramolecularly hydrogen bonded whereas protons NHb and NHd (|Δδ/ΔT| ∼ 4 ppb/K) were exposed to the solvent. For diastereomer II, proton NHa (|Δδ/ΔT| = 2.5 ppb/K) was probably intramolecularly hydrogen bonded whereas other NH protons were exposed to the solvent (Table 1), see: Kessler, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 512-523.
    • (1982) Angew. Chem., Int. Ed. Engl. , vol.21 , pp. 512-523
    • Kessler, H.1
  • 60
    • 0344990547 scopus 로고    scopus 로고
    • note
    • The above results were confirmed performing a parallel conformational search, using molecular dynamics with Iterative Simulated Annealing, see ref 36. This protocol was run five times, employing fully extended starting structures of both compounds (17a and 17b) and AMBER (implemented in DISCOVER 3) as force field. The profiles for the main parameters characterizing γ- and β-turns were similar to those found with the Monte Carlo protocol (data not shown).
  • 65
    • 0345421633 scopus 로고    scopus 로고
    • note
    • Proton 4-H could not be assigned because it is masked by signals corresponding to the major isomer trans-9a.
  • 66
    • 0345421634 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra indicated the presence of rotamers. This fact was not observed for the cis isomer.
  • 67
    • 0344559478 scopus 로고    scopus 로고
    • note
    • Rotamers were observed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.