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Volumn 63, Issue 20, 1998, Pages 6784-6785

Minimal acylase-like peptides. conformational control of absolute stereospecificity

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EID: 0000089981     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981642w     Document Type: Article
Times cited : (149)

References (36)
  • 2
    • 0000085691 scopus 로고    scopus 로고
    • and references therein
    • (b) Johnson, C. R. Ace. Chem. Res. 1998, 31, 333-341 and references therein.
    • (1998) Ace. Chem. Res. , vol.31 , pp. 333-341
    • Johnson, C.R.1
  • 15
    • 0020001240 scopus 로고
    • A general base-type mechanism cannot be excluded. See: Pandit, N. K.; Connors, K. A. J. Pharm. Sci. 1982, 71, 485-491.
    • (1982) J. Pharm. Sci. , vol.71 , pp. 485-491
    • Pandit, N.K.1    Connors, K.A.2
  • 16
    • 0029876822 scopus 로고    scopus 로고
    • For representative, nonenzymatic enantioselective nucleophilic catalysts, see: (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1809-1810
    • Vedejs, E.1    Chen, X.2
  • 22
    • 0029931671 scopus 로고    scopus 로고
    • For comparative examples of the conformational influence of L-Pro vs D-Pro residues in short peptides, see: (a) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975-6985.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 6975-6985
    • Haque, T.S.1    Little, J.C.2    Gellman, S.H.3
  • 25
    • 85034182414 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 26
    • 85050296727 scopus 로고
    • (a) S values were calculated according to the method of Kagan. See: Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330.
    • (1988) Top. Stereochem. , vol.18 , pp. 249-330
    • Kagan, H.B.1    Fiaud, J.C.2
  • 27
    • 85034163365 scopus 로고    scopus 로고
    • Reaction selectivities and conversions were determined in analogy to the method we reported previously. See Supporting Information for details
    • (b) Reaction selectivities and conversions were determined in analogy to the method we reported previously. See Supporting Information for details,
  • 28
    • 0001501830 scopus 로고    scopus 로고
    • The absolute sense of chirality of 3-Ac and 3 was assigned according to the method of Jacobsen. Schaus, S. E.; Larrow, J. F.; Jacobsen, E. N. J. Org. Chem. 1997, 62, 4197-4199.
    • (1997) J. Org. Chem. , vol.62 , pp. 4197-4199
    • Schaus, S.E.1    Larrow, J.F.2    Jacobsen, E.N.3
  • 29
    • 85034181795 scopus 로고    scopus 로고
    • The confonnational phenomena described herein are mirrored by the other peptides in each series, respectively.
    • The confonnational phenomena described herein are mirrored by the other peptides in each series, respectively.
  • 31
    • 84985651996 scopus 로고
    • For an interpretation of chemical shift dependences as a function of temperature in C6D6 solvent, see: Venkatachalapathi, Y. V.; Balaram, P. Biopolymers 1981, 20, 625-628.
    • (1981) Biopolymers , vol.20 , pp. 625-628
    • Venkatachalapathi, Y.V.1    Balaram, P.2
  • 34
    • 85034157611 scopus 로고    scopus 로고
    • The solution IR spectra for la and 2a are consistent with these assignments. See Supporting Information for details.
    • The solution IR spectra for la and 2a are consistent with these assignments. See Supporting Information for details.
  • 35


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