메뉴 건너뛰기




Volumn 73, Issue 23, 2008, Pages 9228-9234

A simple microscale method for determining the relative stereochemistry of statine units

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINES; AMINO ACIDS; CHEMICAL REACTIONS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS;

EID: 57649091688     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8012429     Document Type: Article
Times cited : (26)

References (51)
  • 5
    • 0942277395 scopus 로고    scopus 로고
    • For a review on determining absolute configurations by NMR see
    • For a review on determining absolute configurations by NMR see: Seco, J. M.; Quiñoá, E.; Riguera, R. Chem. Rev. 2004, 7, 17-117.
    • (2004) Chem. Rev , vol.7 , pp. 17-117
    • Seco, J.M.1    Quiñoá, E.2    Riguera, R.3
  • 8
    • 0019469697 scopus 로고    scopus 로고
    • Rinehart, K. L., Jr.; Gloer, J. B.; Hughes, R. G., Jr.; Renis, H. E.; McGovren, J. P.; Swynenberg, E. B.; Stringfellow, D. A.; Kuentzel, S. L.; Li, L. H. Science 1981, 212, 933-935.
    • (a) Rinehart, K. L., Jr.; Gloer, J. B.; Hughes, R. G., Jr.; Renis, H. E.; McGovren, J. P.; Swynenberg, E. B.; Stringfellow, D. A.; Kuentzel, S. L.; Li, L. H. Science 1981, 212, 933-935.
  • 20
    • 21844465721 scopus 로고    scopus 로고
    • The stereochemistry of 24a was determined by conversion to the oxazolidinone derivative through treatment with triphosgene.The stereochemistry was then assigned via analysis of the JH3,H4 coupling constant. See: Wang, M.; Chen, Y.; Lou, L.; Tang, W.; Wang, X.; Shen, J. Tetrahedron Lett. 2005, 46, 5309-5312.
    • The stereochemistry of 24a was determined by conversion to the oxazolidinone derivative through treatment with triphosgene.The stereochemistry was then assigned via analysis of the JH3,H4 coupling constant. See: Wang, M.; Chen, Y.; Lou, L.; Tang, W.; Wang, X.; Shen, J. Tetrahedron Lett. 2005, 46, 5309-5312.
  • 21
    • 85069130017 scopus 로고    scopus 로고
    • A comparison of carbon and proton chemical shifts with the nature of the side chain (polar, nonpolar, aromatic, branched, etc) provided no predictive trend either
    • A comparison of carbon and proton chemical shifts with the nature of the side chain (polar, nonpolar, aromatic, branched, etc) provided no predictive trend either.
  • 22
    • 33845280841 scopus 로고    scopus 로고
    • There are reports of using 3JH3,H4 values for the relative stereochemical assignment of an Ala-Sta derivative (4-methylcarnitine: Comber, R. N.; Brouillette, W. J. J. Org. Chem. 1988 53 1121-1122), but based on our data (see the Supporting Information) this is not a general trend
    • There are reports of using 3JH3,H4 values for the relative stereochemical assignment of an Ala-Sta derivative (4-methylcarnitine: Comber, R. N.; Brouillette, W. J. J. Org. Chem. 1988 53 1121-1122), but based on our data (see the Supporting Information) this is not a general trend
  • 25
    • 85069134528 scopus 로고    scopus 로고
    • At 500 MHz, the 1H NMR spectra for these compounds were second order
    • At 500 MHz, the 1H NMR spectra for these compounds were second order.
  • 26
    • 85069129454 scopus 로고    scopus 로고
    • Spin simulations were done with MestreC 4.9.8.0 in an iterative fashion comparing with the experimental spectra until identical patterns were obtained. Experimental data were used as a constraint in these simulations when possible, i.e., δH3, 2JH2u,H2d, 3JH3,H2d + 3JH3,H2u, ca. δH2.
    • Spin simulations were done with MestreC 4.9.8.0 in an iterative fashion comparing with the experimental spectra until identical patterns were obtained. Experimental data were used as a constraint in these simulations when possible, i.e., δH3, 2JH2u,H2d, 3JH3,H2d + 3JH3,H2u, ca. δH2.
  • 27
    • 85069133914 scopus 로고    scopus 로고
    • A Scifinder Scholar search for the basic carbon skeleton yielded approximately 10 000 compounds, but the utility of this literature NMR data varied greatly. For example, H2-2 was frequently reported as a multiplet spanning a considerable chemical shift range. This indicated the methylene protons were probably diastereotopic (otherwise H2-2 would be a simple doublet), but provided no coupling constant information for comparison.
    • A Scifinder Scholar search for the basic carbon skeleton yielded approximately 10 000 compounds, but the utility of this literature NMR data varied greatly. For example, H2-2 was frequently reported as a multiplet spanning a considerable chemical shift range. This indicated the methylene protons were probably diastereotopic (otherwise H2-2 would be a simple doublet), but provided no coupling constant information for comparison.
  • 29
    • 51749111836 scopus 로고    scopus 로고
    • Zhang et al. have recently reported a new cyclic thiazolyl peptide Phillipmycin containing a statine unit, whose configuration can be correctly predicted with this method. See
    • Zhang et al. have recently reported a new cyclic thiazolyl peptide Phillipmycin containing a statine unit, whose configuration can be correctly predicted with this method. See: Zhang, C.; et al. J. Am. Chem. Soc. 2008, 130, 12102-12110.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 12102-12110
    • Zhang, C.1
  • 30
    • 0035478942 scopus 로고    scopus 로고
    • Andrés, J. M, Pedrosa, R, Pérez, A, Pérez-Encabo, A. Tetrahedron 2001, 57, 8521-8530. This reference also includes two Pro-Stat derivatives in which the ABX pattern appears to be reversed. We have synthesized one of these compounds, the Pro-Stat protected as a tert-butyl ester, and find the NMR data to be consistent with the rest of our data set
    • Andrés, J. M.; Pedrosa, R.; Pérez, A.; Pérez-Encabo, A. Tetrahedron 2001, 57, 8521-8530. This reference also includes two Pro-Stat derivatives in which the ABX pattern appears to be reversed. We have synthesized one of these compounds, the Pro-Stat protected as a tert-butyl ester, and find the NMR data to be consistent with the rest of our data set.
  • 37
    • 0034703342 scopus 로고    scopus 로고
    • Ishida, K, Murakami, M. J. Org. Chem. 2000, 65, 5898-5900, The vicinal coupling constants for the methylene proton signals (δH 2.35 and 2.28) in Table 1 of this reference are transposed. We thank Drs. Ishida, Murakami, and Okada for providing copies of the original 1H NMR spectrum so that we could check these data. The NMR spectra is included in our Supporting Information
    • Ishida, K.; Murakami, M. J. Org. Chem. 2000, 65, 5898-5900, The vicinal coupling constants for the methylene proton signals (δH 2.35 and 2.28) in Table 1 of this reference are transposed. We thank Drs. Ishida, Murakami, and Okada for providing copies of the original 1H NMR spectrum so that we could check these data. The NMR spectra is included in our Supporting Information.
  • 38
    • 10044224781 scopus 로고    scopus 로고
    • Isolation: Nakatani, S.; Kamata, K.; Sato, M.; Onuki, H.; Hirota, H.; Matsumoto, J.; Ishibashi, M. Tetrahedron Lett. 2005, 46, 267-271.
    • Isolation: Nakatani, S.; Kamata, K.; Sato, M.; Onuki, H.; Hirota, H.; Matsumoto, J.; Ishibashi, M. Tetrahedron Lett. 2005, 46, 267-271.
  • 39
    • 37549039089 scopus 로고    scopus 로고
    • Synthesis: Hanazawa, S.; Arai, M.; Li, X.; Ishibashi, M. Bioorg. Med. Chem. Lett. 2008, 18, 95-98.
    • Synthesis: Hanazawa, S.; Arai, M.; Li, X.; Ishibashi, M. Bioorg. Med. Chem. Lett. 2008, 18, 95-98.
  • 40
    • 0034715481 scopus 로고    scopus 로고
    • Isolation: Nakao, Y.; Fujita, M.; Warabi, K.; Matsunaga, S.; Fusetani, N. J. Am. Chem. Soc. 2000, 122, 10462-10463.
    • Isolation: Nakao, Y.; Fujita, M.; Warabi, K.; Matsunaga, S.; Fusetani, N. J. Am. Chem. Soc. 2000, 122, 10462-10463.
  • 41
    • 34547563523 scopus 로고    scopus 로고
    • Synthesis: Konno, H.; Kubo, K.; Makabe, H.; Toshiro, E.; Hinoda, N.; Nosaka, K.; Akaji, K. Tetrahedron 2007, 63, 9502-9513.
    • Synthesis: Konno, H.; Kubo, K.; Makabe, H.; Toshiro, E.; Hinoda, N.; Nosaka, K.; Akaji, K. Tetrahedron 2007, 63, 9502-9513.
  • 42
    • 85069133827 scopus 로고    scopus 로고
    • Occasionally, H2-2 appeared as a simple doublet in the initial proton spectra of 6-24 immediately after silica chromatography. After 24 h in CDCl3, these proton signals were generally resolved.
    • Occasionally, H2-2 appeared as a simple doublet in the initial proton spectra of 6-24 immediately after silica chromatography. After 24 h in CDCl3, these proton signals were generally resolved.
  • 43
    • 85069131808 scopus 로고    scopus 로고
    • Because of this requirement of CDCl3 solubility, data for the deprotected compounds 6-24 were generally not included.
    • Because of this requirement of CDCl3 solubility, data for the deprotected compounds 6-24 were generally not included.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.