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Diastereomerically pure 3 were smoothly isolated by flash chromatography on silica gel.
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83
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0141839533
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3)]Gly peptide"), while the stereochemistry of the other major diastereomers 3b-j was assigned on the basis of their spectral and chemical-physical similarities with 3a. The stereochemistry of 5a, major diastereomer derived from D-Ala-OMe la, was determined by chemical correlation with 3a after cleavage of the oxazolidinone auxiliary.
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note
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Only proline derived pseudo-tripeptide 9d, obtained as a ca. 3:1 mixture of isomers at the peptide bond, and tetrapeptide 10 were isolated as foams.
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103
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0141728246
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note
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These compounds were obtained as described in ref. [7c].
-
-
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104
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0141728245
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note
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b chemical shifts of epimers 13 and 14 seems to be convergent at higher temperature, which is more than reasonable for two closely similar structures.
-
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105
-
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0141728244
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note
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b. (equation presented)
-
-
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106
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0141616323
-
-
note
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Also, for 14 free MD calculations were performed and, after minimization without constraints, many different structures were obtained.
-
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107
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0141728247
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note
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CCDC-204501-204503 (3a, 9a and 9c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44)1223-336-033; or e-mail: deposit@ccdc.cam. ac.uk).
-
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-
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109
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0141504835
-
-
note
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3)]Gly peptides fall within this range, although they are quite large and shifted toward the upper limit value;
-
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-
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110
-
-
0141504834
-
-
note
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3)]Gly peptides incorporate a framework B, mimic of the Gellman's retropeptide unit C (see ref. [19]). This is likely due to the fact that amide and imide carbonyls are much better hydrogen-bond acceptors than carbonyls belonging to ester functions. (equation presented)
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