Alkyl 3-Position Substituents Retard the Isomerization of Prolyl and Hydroxyprolyl Amides in Water

Journal of Organic Chemistry

Volumn 63, Issue 19, 1998, Pages 6572-6578

  Beausoleil, Eric ^a   Sharma, Raman ^a   Michnick, Stephen W ^a   Lubell, William D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000617719     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980673o     Document Type: Article

References (51)

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29. 13C NMR (minor isomer is in parentheses) δ (22) 22.3, 26.4 (26.5), 38.6 (40.5), (56.2) 57.5, 60.6 (62.1), (69.8) 71.2, 172.9 (173.1), (175.1) 175.3.
30. 2 = 0.0737 for all data; GOF = 1.060. The author has deposited the atomic coordinates for the structure of 6 with the Cambridge Crystallographic Data Center. The coordinates can be obtained, on request, from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ, U.K.
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44. The ψ, φ, and ω values for the calculated energy minima of the trans and cis isomers in 1-6 were as follows: 1 trans isomer, 128°, -57°, -179°, 1 cis isomer, 131°, -59°, 0°; 2 trans isomer, 162°, -57°, 177°; 2 cis isomer, 164°, -60°, -6°; 3 trans isomer, 152°, -72°, 180°; 3 cis isomer, 154°, -72°, -1°; 4 trans isomer, 154°, -71°, 180°; 4 cis isomer, 155°, -72°, -2°; 5 trans isomer, 151°, -72°, 180°; 5 cis isomer, 152°, -73°, -2°; 6 trans isomer, 141°, -71°, 180°; 6 cis isomer, 142°, -72°, -2°. Maps constructed for N-acetylproline N'-methylamides 1-6 by plotting the minimum energy value at each 30° interval against the values for the ψ and ω dihedral angles are included in the Supporting Information.
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51. It is interesting to note that the presence of a 4-position hydroxyl group increased the magnitude of the ψ dihedral angle from ψ ≈ 130° to ψ ≈ 153° to ψ ≈ 163° in the minimum energy conformations of the proline amides going from 1 to 3 to 2.