2.5 Analysis summary
Ethyl iso-oleoyl arginate hydrochloride(Fig. 2, structure 1) : yield (76%), light yellow sticky solid; water solubility (4.40%); ATR-FT-IR (cm-1, Fig. 3C): 1736 (-CO 2CH2CH3), 1646 (-CH2CO NH-), 3100-3600 (amine);1H-NMR (CDCl3, 600 MHz, Fig. 5B): δ 1.58 (m, CH3 CH=CH-, 3H), 2.25 (t, -CH2 CONH-, 2H), 4.2 (t, -CO2CH2 CH3, 2H), 4.4 (m, -CH NH-), 5.38 (m, CH3CH =CH -, 2H), 7.25 (m, -CH2CONH -, 1H); 13C NMR (CDCl3, 150 MHz, Fig. 6B): δ 14 (s,C H3CH=CH-), 36 (s, -C H2CONH-), 51.93 (s, -C HNH-), 52.59 (s, -C HNH-), 130 (m, CH3C H=C H-), 158 (s, -H2NC NH-), 172.16 (s, -C O2CH2CH3), 172.64 (s, -C O2CH2CH3), 174.5 (s, -CH2C ONH-); LC-MS-Tof (m/z ): 467.3194 [M + H]+; MW (g/mol): 466.39.
Ethyl iso-stearoyl arginate hydrochloride (Fig. 2, structure 2) : yield (80%), light yellow sticky solid; water solubility (0.46%); ATR-FT-IR (cm-1, Fig. 3D): 1734 (-CO 2CH2CH3), 1648 (-CH2CO NH-), 3100-3600 (amine),1H-NMR (CDCl3, 600 MHz, Fig. 5C): δ 0.82 (m, CH3 CHCH2-, 3H), 2.25 (t, -CH2 CONH-, 2H), 4.18 (t, -CO2CH2 CH3, 2H), 4.42 (m, -CH NH-), 7.25 (m, -CH2CONH -, 1H);13C NMR (CDCl3, 150 MHz, Fig. 6C): δ 14? (s, C H3CHCH2-), 36 (s, -C H2CONH-), 51.93 (s, -C HNH-), 52.59 (s, -C HNH-), 157.5 (s, -H2NC NH-), 172 (s, -C O2CH2CH3), 172.5 (s, -C O2CH2CH3), 174.5 (s, -CH2C ONH-); LC-MS-Tof (m/z ): 469.4872 [M + H]+; MW (g/mol): 468.40.
Ethyl n-oleoyl arginate hydrochloride (Fig. 2, structure 3) : yield (89%), light yellow sticky solid; water solubility (4.40%); ATR-FT-IR (cm-1, SFig. 1C): 1736 (-CO 2CH2CH3), 1651, (-CH2CO NH-), 3000-3600 (amine);1H-NMR (CDCl3, 600 MHz, Fig. 5D): δ 2.25 (t, -CH2 CONH-, 2H), 4.2 (t, -CO2CH2 CH3, 2H), 4.4 (m, -CH NH-), 5.15 (m, -CH=CH-, 2H), 7.25 (m, -CH2CONH -, 1H); 13C NMR (CDCl3, 150 MHz, Fig. 6D): δ 36 (s, -C H2CONH-), 52 (s, -C HNH-), 130 (s, -CH=CH-), 157 (s, -H2NC NH-), 172.2 (s, -C O2CH2CH3), 174.5 (s, -CH2C ONH-); LC-MS-Tof (m/z ): 467.4587 [M + H]+; MW (g/mol): 466.39.
Ethyl n-stearoyl arginate hydrochloride (Fig. 2, structure 4) : yield (85%), light yellow solid; insoluble in water; ATR-FT-IR (cm-1, Fig. 1D): 1752 (-CO 2CH2CH3), 1642, (-CH2CO NH-), 3000-3600 (amine);1H-NMR (CD3OH, 600 MHz, Fig. 5E): δ 2.25 (t, -CH2 CONH-, 2H), 4.2 (t, -CO2CH2 CH3, 2H), 4.4 (m, -CH NH-); 13C NMR (CD3OH, 150 MHz, Fig. 6E): δ 36 (s, -C H2CONH-), 52.2 (s, -C HNH-), 158 (s, -H2NC NH-), 172.5 (s, -C O2CH2CH3), 176 (s, -CH2C ONH-); LC-MS-Tof (m/z ): 469.4907 [M + H]+; MW (g/mol): 468.40.
Ethyl n-lauroyl arginate hydrochloride(Fig. 2, structure 5 ): yield (91%), white solid; water solubility (4.40%); ATR-FT-IR (cm-1, Fig. 4C): 1736 (-CO 2CH2CH3), 1645 (-CH2CO NH-), 3100-3600 (amine);1H-NMR (CDCl3, 600 MHz, Fig. 5A): δ 2.25 (t, -CH2 CONH-, 2H), 4.2 (t, -CO2CH2 CH3, 2H), 4.4 (m, -CH NH-), 7.25 (m, -CH2CONH -, 1H);13C NMR (CDCl3, 150 MHz, Fig. 6A): δ 36 (s, -C H2CONH-), 52 (s, -C HNH-), 158.5 (s, -H2NC NH-), 172 (s, -C O2CH2CH3), 174.5 (s, -CH2C ONH-); LC-MS-Tof (m/z ): 385.3150 [M + H]+; MW (g/mol): 384.31.