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Table 1 Characteristics of the obtained 3-methoxymethyl derivatives

From: Pregnenolone and progesterone production from natural sterols using recombinant strain of Mycolicibacterium smegmatis mc2 155 expressing mammalian steroidogenesis system

Name and Chemical Structure

High-Performance Liquid Chromatography (HPLC), Mass-Spectrometry (MS), 1H- and 13C-Nuclear Magnetic Resonance Spectroscopy Data

Retention time (Rt) 16.53 (mobile phases I); 1H-NMR (CDCl3) δ: 5.36 (m, 1H, 6-H), 4.69 (s, 2H, 3-OCH2OCH3), 3.42 (m, 1H, 3α-H), 3.37 (s, 3H, 3-OCH2OCH3), 1.01 (s, 3H, 19-CH3), 0.91 (d, J = 6.5 Hz, 3H, 21-CH3), 0.87 (d, J = 6.6 Hz, 3H, 26(27)-CH3), 0.86 (d, J = 6.6 Hz, 3H, 26(27)-CH3), 0.69 (s, 3H, 18-CH3). 13C-NMR (CDCl3) δ: 140.7 (C-5), 121.7 (C-6), 94.7 (3-OCH2OCH3), 76.9 (C-3), 56.7, 56.1, 55.2, 50.1, 42.3, 39.7, 39.5, 37.2, 36.7, 36.2, 35.8, 31.9, 31.8, 28.9, 28.2, 28.0, 24.3, 23.8, 22.8, 22.6, 21.0, 19.4, 18.7, 11.8

Rt 14–17.5 (mobile phases I); 1H-NMR for a mixture of 3-methoxymethyl-sterols (CDCl3) δ: 5.36 (m, 1H, 6-H), 5.18–5.12 (m, 0.3H, 22(23)-H), 5.04–4.98 (m, 0.3H, 22(23)-H),4.69 (s, 2H, 3-OCH2OCH3), 3.43 (m, 1H, 3α-H), 3.37 (s, 3H, 3-OCH2OCH3), 1.03–0.69 (m, 25H, 19-CH3, 21-CH3, 242-CH3, 241-CH3, 26-CH3, 27-CH3, 18-CH3). 13C-NMR for a mixture of 3-methoxymethyl-sterols (CDCl3) δ: 140.7 (C-5), 138.3 (C-22), 129.2 (C-23), 121.7 (C-6), 94.6 (3-OCH2OCH3), 76.9 (C-3), 56.8, 56.7, 56.0, 55.9, 55.1, 51.2, 50.1, 45.8, 42.3, 42.2, 40.5, 39.7, 39.6, 39.5, 37.2, 36.7, 36.1, 35.9, 33.9, 33.7, 32.4, 31.9, 31.9, 31.4, 30.2, 29.1, 28.9, 28.2, 26.0, 25.4, 24.3, 24.3, 23.0, 21.2, 21.1, 21.0, 20.2, 19.8, 19.3, 19.0, 18.8, 18.7, 18.2, 15.4, 15.3, 12.2, 12.0, 12.0, 11.8

Rt 3.77 (mobile phases I); 1H-NMR (CDCl3) δ: 5.36 (m, 1H, 6-H), 4.69 (s, 2H, 3-OCH2OCH3), 3.43 (m, 1H, 3α-H), 3.37 (s, 3H, 3-OCH2OCH3), 2.53 (m, 1H. 17α-H), 2.13 (s, 3H, 21-CH3), 1.01 (s, 3H, 19-CH3), 0.63 (s, 3H, 18-CH3). 13C-NMR (CDCl3) δ: 209.5 (C-20), 140.7 (C-5), 121.4 (C-6), 94.6 (3-OCH2OCH3), 76.8 (C-3), 63.7, 56.8, 55.1, 50.0, 43.9, 39.5, 38.8, 37.2, 36.7, 31.8, 31.7, 31.5, 28.8, 24.4, 22.7, 21.0, 19.3, 13.2

Rt 3.33 (mobile phases I); 1H-NMR (CDCl3) δ: 5.39 (m, 1H, 6-H), 4.69 (s, 2H, 3-OCH2OCH3), 3.43 (m, 1H, 3α-H), 3.38 (s, 3H, 3-OCH2OCH3), 1.04 (s, 3H, 19-CH3), 0.89 (s, 3H, 18-CH3). 13C-NMR (CDCl3) δ: 221.1 (C-17), 140.9 (C-5), 120.9 (C-6), 94.7 (3-OCH2OCH3), 76.7 (C-3), 55.2, 51.7, 50.2, 47.5, 39.5, 37.1, 36.8, 35.8, 31.4, 31.3, 30.7, 28.8, 21.8, 20.3, 19.4, 13.5

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