Frömmel J. et al.: N-acyl-ω-aminoaldehydes are efficient substrates of plant aminoaldehyde dehydrogenases

Supplementary file 1

A list of abbreviations for names of the compounds:

Propi-APAL / N-propionyl derivative of 3-aminopropanal
Butyr-APAL / N-butyryl derivative of 3-aminopropanal
2-Met-Propi -APAL / N-(2-methylpropionyl) derivative of 3-aminopropanal
Valer-APAL / N-valeryl derivative of 3-aminopropanal
2-Met-Butyr-APAL / N-(2-methylbutyryl) derivative of 3-aminopropanal
3-Met-Butyr-APAL / N-(3-methylbutyryl) derivative of 3-aminopropanal
2,2-diMet-Propi-APAL / N-(2,2-dimethylpropionyl) derivative of 3-aminopropanal
Adip-APAL / N-adipoyl derivative of 3-aminopropanal
Propi-ABAL / N-propionyl derivative of 4-aminobutanal
Butyr-ABAL / N-butyryl derivative of 4-aminobutanal
2-Met-Propi-ABAL / N-(2-methylpropionyl) derivative of 4-aminobutanal
Valer-ABAL / N-valeryl derivative of 4-aminobutanal
2-Met-Butyr-ABAL / N-(2-methylbutyryl) derivative of 4-aminobutanal
3-Met-Butyr-ABAL / N-(3-methylbutyryl) derivative of 4-aminobutanal
2,2-diMet-Propi-ABAL / N-(2-methylpropionyl) derivative of 4-aminobutanal

On the following pages, 1H and 13C NMR spectral data for synthetic N-acyl-ω-aminoaldehydes are provided.

N-(3,3-Diethoxypropyl)propanamide i. e. diethylacetal of Propi-APAL

1H (300 MHz, DMSO-d6): δ ppm - 0.97 (t, J=7.59 Hz, 3 H) 1.09 (t, J=7.04 Hz, 6 H) 1.62 (q, J=6.71 Hz, 2 H) 2.03 (q, J=7.68 Hz, 2 H) 3.04 (q, J=6.77 Hz, 2 H) 3.33 - 3.47 (m, 2 H) 3.47 - 3.62 (m, 2 H) 4.48 (t, J=5.58 Hz, 1 H) 7.71 (br. s., 1 H)

13C (75 MHz, DMSO-d6): δ ppm - 10.5, 15.9, 29.0, 33.9, 35.2, 61.2, 101.0, 173.2

N-(4,4-Diethoxybutyl)propanamide i.e. diethylacetal of Propi-ABAL

1H (500 MHz, CDCl3): δ ppm - 1.15 (t, J = 8.0 Hz, 3H), 1.20 (t, J = 7.0 Hz, 6H), 1.56-1.61 (m, 2H), 1.62-1.67 (m, 2H), 2.18 (q, J = 8.0 Hz, 2H), 3.37 (q, J = 6.5 Hz, 2H), 3.46-3.52 (m, 2H), 3.62-3.68 (m, 2H), 4.48 (t, J = 5.0 Hz, 1H), 5.68 (bs, 1H)

13C (125 MHz, CDCl3):10.0, 15.4, 24.7, 29.8, 31.1, 39.2, 61.5, 102.8, 173.7

N-(3,3-Diethoxypropyl)butanamide i.e. diethylacetal of Butyr-APAL

1H (300 MHz, DMSO-d6): δ ppm - 0.83 (t, J=7.32 Hz, 3 H) 1.09 (t, J=7.04 Hz, 6 H) 1.38 - 1.54 (m, 2 H) 1.62 (q, J=6.71 Hz, 2 H) 2.00 (t, J=7.32 Hz, 2 H) 3.04 (q, J=6.53 Hz, 2 H) 3.31 - 3.47 (m, 2 H) 3.48 - 3.62 (m, 2 H) 4.47 (t, J=5.67 Hz, 1 H) 7.60 - 7.84 (m, 1 H)

13C (75 MHz, DMSO-d6): δ ppm - 14.1, 15.9, 19.2, 34.0, 35.1, 37.9, 61.2, 101.0, 172.3

N-(4,4-Diethoxybutyl)butanamide i.e.diethylacetal of Butyr-ABAL

1H (500 MHz, CDCl3): δ ppm - 0.91 (t, J = 7.5 Hz, 3H), 1.18 (t, J = 7.5 Hz, 6H), 1.54 – 1.59 (m, 2H), 1.60 – 1.65 (m, 4H), 2.11 (t, J = 7.5 Hz, 2H), 3.25 (q, J = 7.0 Hz, 2H), 3.44-3.50 (m, 2H), 3.60-3.66 (m, 2H), 4.46 (t, J = 6.0 Hz, 1H), 5.67 (bs, 1H)

13C (125 MHz, CDCl3): δ ppm - 13.8, 15.4, 19.3, 31.1, 38.8, 39.2, 61.5, 102.7, 173.0

N-(3,3-Diethoxypropyl)pentanamide i.e. diethylacetal of Valer-APAL

1H (500 MHz, CDCl3): δ ppm - 0.85 – 0.89 (m, 3H), 1.16 – 1.20 (m, 6H), 1.27-1.31 (m, 2H), 1.53-1.58 (m, 2H), 1.76-1.80 (m, 2H), 2.08-2.12 (m, 2H), 3.29-3.33 (m, 2H), 3.44-3.49 (m, 2H), 3.62-3.66 (m, 2H), 4.50-4.52 (m, 1H), 6.19 (bs, 1H)

13C (125 MHz, CDCl3): δ ppm - 13.8, 15.4, 22.4, 27.9, 32.9, 35.4, 36.7, 62.0, 102.7, 173.0

N-(4,4-Diethoxybutyl)pentanamide i.e. diethylacetal of Valer-ABAL

1H (500 MHz, CDCl3): δ ppm - 0.89 (t, 3H, J = 7.25 Hz), 1.19 (t, 6H, J = 7.20 Hz), 1.32 (sext., 2H, J = 7.20 Hz), 1.54-1.65 (m, 6H), 2.12 – 2.15 (app. dd, 2H), 2.25 (q, 2H, J = 6.0 Hz), 3.45-3.49 (m, 2H), 3.61-3.66 (m, 2H), 4.46 (t, 1H, J = 5.50 Hz), 5.65 (bs, 1H)

13C (125 MHz, CDCl3): δ ppm - 13.8, 15.4, 22.5, 24.6, 27.9, 31.0, 36.7, 39.2, 61.5, 102.7, 173.2

N-(3,3-Diethoxypropyl)-2-methylpropanamide i. e. diethylacetal of 2-Met-Propi-APAL

1H (500 MHz, CDCl3): δ ppm - 1.10 – 1.21 (m, 12H), 1.78 – 1.81 (m, 2H), 1.27-1.30 (m, 1H), 3.32-3.34 (m, 2H), 3.46-3.50 (m, 2H), 3.62-3.68 (m, 2H), 4.52-4.54 (m, 1H), 6.21 (bs, 1H)

13C (125 MHz, CDCl3): δ ppm - 15.4, 19.6, 32.9, 35.4, 35.7, 62.1, 102.8, 176.8

N-(4,4-Diethoxybutyl)-2-methylpropanamide i. e. diethylacetal of 2-Met-Propi-ABAL

1H (500 MHz, CDCl3): δ ppm - 1.11 (d, 6H, J = 6.7 Hz), 1.18 (t, 6H, J = 7 Hz), 1.54-1.58 (m, 2H), 1.60-1.64 (m, 2H), 2.30 (sept., 1H, J = 6.7 Hz), 3.24 (q, 2H, J = 6 Hz), 3.45-3.49 (m, 2H), 3.59-3.65 (m, 2H), 4.46 (t, 1H, J = 5.5 Hz), 5.68 (bs, 1H)

13C (125 MHz, CDCl3): δ ppm -15.4, 19.7, 24.6, 31.0, 35.8, 39.1, 61.5, 102.7, 177.0.

N-(3,3-Diethoxypropyl)-2,2-dimethylpropanamide i. e. diethylacetal of 2,2-diMet-Propi-APAL

1H (500 MHz, CDCl3): δ ppm - 1.16 (s, 9H), 1.21 (t, 6H, J = 7 Hz), 1.79-1.83 (m, 2H), 3.33-3.36 (m, 2H), 3.47-3.53 (m, 2H), 3.65-3.71 (m, 2H), 4.55 (t, 1H, J = 5 Hz), 6.44 (bs, 1H)

13C (125 MHz, CDCl3): δ ppm - 15.4, 27.6, 32.9, 35.5, 38.6, 62.2, 103.2, 178.2

N-(4,4-Diethoxybutyl)-2,2-dimethylpropanamide i. e. diethylacetal of 2,2-diMet-Propi-ABAL

1H (500 MHz, CDCl3): δ ppm - 1.17 (s, 9H), 1.19 (t, 6H, J = 7 Hz), 1.55-1.65 (m, 4H), 3.23-3.26 (m, 2H), 3.46-3.49 (m, 2H), 3.60-3.66 (m, 2H), 4.48 (t, 1H, J = 5 Hz), 5.79 (bs, 1H)

13C (125 MHz, CDCl3): δ ppm - 15.4, 24.6, 27.7, 30.9, 39.2, 61.4, 102.7, 178.4

N-(3,3-Diethoxypropyl)-2-methylbutanamide i. e. diethylacetal of 2-Met-Butyr-APAL

1H (500 MHz, CDCl3): δ ppm - 0.88 (t, 3H, J = 8 Hz), 1.10 (d, 3H, J = 6.7 Hz), 1.21 (t, 6H, J = 7.3 Hz), 1.60 -1.66 (m, 2H), 1.81 (q, 2H, J = 6 Hz), 2.01-2.06 (m, 1H), 3.34-3.38 (m, 2H), 3.48-3.53 (m, 2H), 3.64-3.69 (m, 2H), 5.55 (t, 1H, J = 5 Hz), 6.12 (bs, 1H)

13C (125 MHz, CDCl3): δ ppm - 12.0, 15.4, 17.5, 27.4, 33.0, 35.3, 43.4, 62.1, 102.8, 176.2

N-(4,4-Diethoxybutyl)-2-methylbutanamide i. e. diethylacetal of 2-Met-Butyr-ABAL

1H (500 MHz, CDCl3): δ ppm - 0,85 (t, 3H, J = 7.3 Hz), 1.11 (d, 3H, J = 6.7 Hz), 1.19 (t, 6H, J = 7 Hz), 1.38-1.43 (m, 1H), 1.56-1.65 (m, 6H), 2.02-2.07 (m, 1H), 3.24-3.29 (m, 2H), 3.46-3.51 (m, 2H), 3.60-3.67 (m, 2H), 4.47 (t, 1H, J = 5 Hz), 5.59 (bs, 1H)

13C (125 MHz, CDCl3): δ ppm - 12.0, 15.4, 17.6, 24.7, 27.4, 31.0, 39.0, 43.4, 61.5, 102.7, 176.4

N-(3,3-Diethoxypropyl)-3-methylbutanamide i. e. diethylacetal of 3-Met-Butyr-APAL

1H (500 MHz, CDCl3): δ ppm - 0.93 (d, 6H, J = 6.7 Hz), 1.21 (t, 6H, J = 7 Hz), 1.72-1.83 (m, 2H), 1.99 (d, 2H, J = 7.3 Hz), 2.06-2.10 (m, 1H), 3.34-3.37 (m, 2H), 3.48-3.52 (m, 2H), 3.63-3.70 (m, 2H), 4.55 (t, 1H, J = 5 Hz), 6.07 (bs, 1H)

13C (125 MHz, CDCl3): δ ppm - 15.4, 22.6, 26.2, 33.0, 35.4, 46.5, 62.0, 102.7, 172.3

N-(4,4-Diethoxybutyl)-3-methylbutanamide i. e. diethylacetal of 3-Met-Butyr-ABAL

1H (500 MHz, CDCl3): δ ppm - 0.93 (d, 6H, J = 6.7 Hz), 1.19 (t, 6H, J = 7 Hz), 1.54-1.66 (m, 4H), 2.00 (d, 2H, J = 7.3 Hz), 2.07-2.12 (m, 1H), 3.24-3.28 (m, 2H), 3.45-3.51 (m, 2H), 3.60-3.67 (m, 2H), 4.47 (t, 1H, J = 5 Hz), 5.58 (bs, 1H)

13C (125 MHz, CDCl3): δ ppm - 15.4, 22.5, 24.7, 26.2, 31.1, 38.7, 39.2, 46.4, 61.5, 102.7, 172.5

Methyl 6-[(3,3-diethoxypropyl)amino]-6-oxohexanoate i.e. diethylacetal of methyl-esterified Adip-APAL

1H (500 MHz, CDCl3): δ ppm - 1.06 (t, 6H, J = 7 Hz), 1.41-1.48 (m, 4H), 1.58 (q, 2H, J = 6,7 Hz), 1.98 – 2.01 (m, 2H), 2.24 – 2.26 (m, 2H), 3.00 (q, 2H, J = 6,7 Hz), 3.34-3.40 (m, 2H), 3.48-3.51 (m, 2H), 3.53 (s, 3H), 4.44 (t, 1H, J = 5,5 Hz), 7.73 (bt, 1H, J = 5 Hz)

13C (125 MHz, DMSO-d6): δ ppm - 15.8, 24.5, 25.2, 33.5, 33.9, 35.1, 35.5, 51.7, 61.2, 100.9, 172.2, 173.7

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