Molecules 2009, 14
4058
1
N-Stearoyl-L-proline (3). Yield 50%; white solid; m.p. 87-89 °C; [α] 22 : +32.1° (c 1.0, CHCl3); H-
D
NMR: δ (ppm) 4.81-4.66 (m, 5H of pyrrolidine), 3.22 (m, 2H of pyrrolidine), 2.13 (t, 2H, J = 3.5 Hz,
13
CH2CON), 1.55 (m, 2H, CH2), 1.23 (m, 28H, 14 × CH2), 0.89 (t, 3H, J = 7 Hz, CH3); C-NMR: δ
(ppm) 174.7, 174.2 (2 × C=O, acid and amide), 61.7 (N-CH of pyrrolidine), 53.4 (N-CH2 of
pyrrolidine), 37.3(CH2), 36.4 (CH2-amide), 31.9 (CH2), 29.7-29.1(13 × CH2), 25.5 (CH2-pyrrolidine),
22.6 (CH2-pyrrolidine), 14.1 (CH3); ESI-MS: [M+Na]+ m/z 404.2.
N-Stearoyl-L-tyrosine (4). Yield 50%; white solid; m.p. 134-136 °C; [α]18 : +41.7° (c 1.0, CH3OH); 1H-
D
NMR: δ (ppm) 6.99 (d, J = 10.4 Hz, 2H of Ph), 6.73 (d, J = 10.2 Hz, 2H of Ph), 5.94 (s, 1H, NH), 4.82
(t, 1H, J = 6.0 Hz, CHN), 3.1 (m, 2H, CH2Ph), 2.17 (t, 2H, J = 7.8 Hz, CH2CON), 1.56 (m, 2H, CH2),
13
1.26 (m, 28H, 14 × CH2), 0.88 (t, 3H, J = 6.8 Hz, CH3); C-NMR: δ (ppm) 174.1,173.9 (2 × C=O,
acid and amide), 155.3 (C-OH of Ph), 133.5(i-C of Ph),130.4 (2 × o-CH of Ph), 115.8 (2 × m-CH of
Ph), 53.4 (CHN), 36.8 (CH2Ph), 36.5 (CH2-amide), 31.9 (CH2), 31.5 (CH2), 29.7-29.2 (12 × CH2), 25.6
(CH2), 22.6 (CH2), 14.0 (CH3); ESI-MS: [M+1]+ m/z 448.2.
1
N-stearoyl-L-serine (5). Yield 60%; white solid; m.p. 100-102 °C; [α]19 : +21.2° (c 1.0, CH3OH); H-
D
NMR (CD3OD): δ (ppm) 4.48 (t, 1H, J = 4.4 Hz, N-CH), 3.86 (m, 2H, CH2O), 2.26 (t, 2H, J = 7.4 Hz,
13
CH2CON), 1.62 (m, 2H, CH2), 1.28 (m, 28H, 14 × CH2), 0.89 (t, 3H, J = 6.8 Hz, CH3); C-NMR
(CD3OD): δ (ppm) 176.7, 173.8 (2 × C=O, acid and amide), 63.3 (CH2O), 56.3 (CHN), 37.2 (CH2-
amide), 33.3 (CH2), 31.1-30.6 (12 × CH2), 27.1 (CH2), 24.0 (CH2), 14.7 (CH3); ESI-MS: [M+1]+ m/z
372.1.
N-Stearoyl-L-threonine (6). Yield 56%; white solid; m.p. 62-64 °C; [α] 22 : +12.5° (c 0.92, CH3OH);
D
1H-NMR (CD3OD): δ (ppm) 6.8 (s, 1H, NH), 4.51 (d, 1H, J = 7.8 Hz, CHN), 4.43 (s, 1H, CHO), 2.3 (t,
2H, J = 7.4 Hz, CH2CON), 1.63 (d, 2H, J = 6.7 Hz, CH2), 1.25 (m, 28H, 14 × CH2), 1.21 (d, 3H, J =
6.0 Hz, CH3), 0.88 (dd, 3H, J1 = 6.7, J2 = 7.0 Hz, CH3); 13C-NMR (CD3OD): δ (ppm) 177.2, 174.1 (2 ×
C=O , acid and amide), 66.5 (CHO), 59.6 (CHN), 36.9 (CH2-amide), 34.2 (CH2), 30.3-29.6 (12 ×
CH2), 26.1 (CH2), 23.3 (CH2), 17.5 (CH3), 14.1 (CH3); ESI-MS: [M+1]+ m/z 389.2.
N-Stearoyl-L-tryptophan (7). Yield 30%; brown solid; m.p. 88-90 °C; [α] 20 : +28° (c 1.0, CHCl3);
D
1HNMR: δ (ppm) 8.37 (s, 1H, NH of indole), 7.54 (d, 1H, J = 7.8 Hz, N-CH of indole), 7.3-6.96 (m,
4H, Ph-H of indole), 6.14 (d, 1H, J = 7.6 Hz, NH), 4.93 (m, 1H, CHN), 3.32 (m, 2H, CH2-indole), 2.07
(t, 2H, J = 7.4 Hz, CH2CON), 1.48 (m, 2H, CH2), 1.25 (m, 28H, 14 × CH2), 0.88 (t, 3H, J = 7 Hz,
13
CH3); CNMR: δ (ppm) 175.1, 174.3 (2 × C=O , acid and amide), 136.1 (N-C of indole),127.8 (C,
indole),123.2 (N-CH of indole),122.2,119.7 (2 × CH, Ph of indole),118.4 (C of indole),111.4,
109.5 (2 × CH, Ph of indole), 53.3 (CHN), 36.4(CH2-amide), 31.9 (CH2-indole), 29.7-27.1 (13 × CH2),
25.4 (CH2), 22.6 (CH2), 14.1 (CH3);ESI-MS: [M+1]+ m/z 471.2.
1
N-Stearoyl-L-leucine (8). Yield 49%; white solid; m.p. 95-97 °C; [α] 20 : −10.3° (c 1.0, CHCl3); H-
D
NMR: δ (ppm) 5.9 (m, 1H, NH), 4.62 (m, 1H, CHN), 2.23 (t, 2H, J = 7.5 Hz, CH2CON), 1.72 (m, 2H,
CH2), 1.62 (m, 2H, CH2), 1.60 (m, 1H, CH), 1.27 (m, 28H, 14 × CH2), 0.95 (d, 6H, J = 4.3 Hz,
2×CH3), 0.88 (t, 3H, J = 7 Hz, CH3); 13C-NMR: δ (ppm) 176.1, 174.1 (2 × C=O, acid and amide), 50.9