TABLE 1.
N-Acyl Aromatic Amino Acids Identified from Living Systems.
| l-Amino Acids a | |||||
|---|---|---|---|---|---|
| N-Acyl Group | Phe | Tyr | Trp | His | References |
| Acetyl [CH3-CO | D | D,Q | D | D,Q | O’Dowd et al. (1988) |
| O’Dowd et al. (1992) | |||||
| Togashi et al. (1998) | |||||
| Tanaka et al. (2015) | |||||
| Yu et al. (2014) | |||||
| Wishart et al. (2018) | |||||
| Propionyl [CH3-CH2-CO-] | NF | NF | NF | NF | |
| Lactoyl [CH3-CH(OH)-CO-] | D | D | NF | NF | Pietrowska et al. (2018) |
| Bonte et al. (2019) | |||||
| Qian et al. (2021) | |||||
| Malonyl [HOOC-CH2-CO-] | D | D | D | NF | Feldberg et al. (2018) |
| Obianyo et al. (2015) | |||||
| Farag and Shakour, (2019) | |||||
| Butyryl [CH3-CH2-CH2-CO-] | NF | D,Q | NF | NF | Hammerl et al. (2017) |
| Succinoyl [HOOC-CH2-CH2-CO-] | NF | NF | D,Q | NF | Yu et al. (2014) |
| α-Malyl [HOOC-CH(OH)-CH2-CO-] | NF | D | D,Q | NF | Yu et al. (2014) |
| Feldberg et al. (2018) | |||||
| β-Malyl [HOOC-CH2-CH-(OH)-CO-] | NF | NF | D,Q | NF | Yu et al. (2014) |
| Crotonyl [CH3-CH = CH-CO-, trans] | NF | NF | NF | NF | |
| Isocrotonyl [CH3-CH = CH-CO-, cis] | NF | NF | NF | NF | |
| Isobutyryl [(CH3)2-CH-CO-] | NF | NF | NF | NF | |
| Pentanoyl (Valeroyl) [CH3-(CH2)3-CO-] | NF | NF | NF | NF | |
| Isovaleroyl [(CH3)2-CH-CH2-CO-] | D | D | D | D | Loots et al. (2005) |
| Pivaloyl [(CH3)3-C-CO-] | NF | NF | NF | NF | |
| Hexanoyl (Caproyl) [CH3-(CH2)4-CO-] | NF | D,Q | NF | D | Hammerl et al. (2017) |
| Tørring et al. (2017) | |||||
| Heptanoyl [CH3-(CH2)5-CO-] | NF | NF | NF | NF | |
| Octanoyl (Capryloyl) [CH3-(CH2)6-CO-] | NF | D,Q | D | D | Brady and Clardy (2000) |
| Brady et al. (2004) | |||||
| Hammerl et al. (2017) | |||||
| Tørring et al. (2017) | |||||
| Nonanoyl (Pelargonoyl) [CH3-(CH2)7-CO-] | NF | D | NF | NF | Brady and Clardy (2000) |
| Brady et al. (2004) | |||||
| Decanoyl [CH3-(CH2)8-CO-] | NF | D | NF | D | Brady and Clardy (2000) |
| Brady et al. (2004) | |||||
| Tørring et al. (2017) | |||||
| Decenoyl [CH3-(CH2)6-CH = CH-CO-, 2-cis] | NF | NF | NF | D | Brady et al. (2004) |
| [CH3-(CH2)6-CH = CH-CO-, 2-trans] | NF | NF | NF | D | Tørring et al. (2017) |
| [CH3-(CH2)5-CH = CH-CH2-CO-, 3-cis] | NF | NF | NF | D | |
| (2-Hexylcyclopropyl)acetyl [cis-cascarilloyl) [CH3-(CH2)5-cyclopropyl-CH2-CO-] | NF | NF | NF | D | Tørring et al. (2017) |
| Undecanoyl [CH3-(CH2)9-CO-] | NF | D | NF | NF | Brady and Clardy (2000) |
| Brady et al. (2004) | |||||
| Lee et al. (2019) | |||||
| Lauroyl [CH3-(CH2)10-CO-] | D | D | NF | NF | Brady and Clardy (2000) |
| Brady et al. (2004) | |||||
| Yeo et al. (2007) | |||||
| Craig and Brady (2011) | |||||
| Lee et al. (2019) | |||||
| Tridecanoyl [CH3-(CH2)11-CO-] | D | D | NF | NF | Brady and Clardy (2000) |
| Brady et al. (2004) | |||||
| Lee et al. (2019) | |||||
| 11-Methyldodecanoyl [(CH3)2-CH-(CH2)9-CO-] | D | NF | NF | NF | Craig and Brady (2011) |
| Myristoyl [CH3-(CH2)12-CO-] | D,Q | D | D | NF | Brady et al. (2004) |
| Clardy and Brady (2007) | |||||
| Long et al. (2016) | |||||
| Thies et al. (2016) | |||||
| Lee et al. (2019) | |||||
| Myristoleoyl [CH3-(CH2)3-CH = CH-(CH2)7-CO-, cis] | NF | NF | NF | NF | |
| 7-Tetradecenoyl [CH3-(CH2)5-CH = CH-(CH2)5-CO-, cis] | NF | D | NF | NF | Brady and Clardy (2000) |
| Pentadecanoyl [CH3-(CH2)13-CO-] | D | D | NF | NF | Brady and Clardy (2000) |
| Brady et al. (2004) | |||||
| Clardy and Brady (2007) | |||||
| Lee et al. (2019) | |||||
| 8-Pentadecenoyl [CH3-(CH2)5-CH = CH-(CH2)6-CO-, cis] | NF | D | NF | NF | Brady and Clardy (2000) |
| Palmitoyl [CH3-(CH2)14-CO-] | D,Q | D,Q | D,Q | D | Brady and Clardy (2000) |
| Brady et al. (2004) | |||||
| Brady and Clardy (2005) | |||||
| Clardy and Brady (2007) | |||||
| Tan et al. (2010) | |||||
| Tortoriello et al. (2013) | |||||
| Leishman et al. (2016) | |||||
| Long et al. (2016) | |||||
| Ren et al. (2019) | |||||
| Berman et al. (2020) | |||||
| Palmitoleoyl [CH3-(CH2)5-CH = CH-(CH2)7-CO-, cis] | NF | D | D | NF | Brady and Clardy (2000) |
| Brady and Clardy (2005) | |||||
| Heptadecanoyl (Margaroyl) [CH3-(CH2)15-CO-] | NF | D | NF | NF | Brady et al. (2004) |
| Stearoyl [CH3-(CH2)16-CO-] | D,Q | D,Q | D,Q | NF | Tan et al. (2010) |
| Tortoriello et al. (2013) | |||||
| Leishman et al. (2016) | |||||
| Qi et al. (2017) | |||||
| Petroselinoyl [CH3-(CH2)10-CH = CH-(CH2)4-CO-, cis] | NF | NF | NF | NF | |
| Oleoyl [CH3-(CH2)7-CH = CH-(CH2)7-CO-, cis] | D,Q | D,Q | D,Q | D | Tan et al. (2010) |
| Tortoriello et al. (2013) | |||||
| Leishman et al. (2016) | |||||
| Kim et al. (2020) | |||||
| Zhou et al. (2020) | |||||
| Elaidoyl [CH3-(CH2)7-CH = CH-(CH2)7-CO-, trans] | NF | NF | NF | NF | |
| cis-Vaccenoyl [CH3-(CH2)5-CH = CH-(CH2)9-CO-, cis] | NF | D | NF | NF | Brady and Clardy (2000) |
| Vaccenoyl [CH3-(CH2)5-CH = CH-(CH2)9-CO-, trans] | NF | NF | NF | NF | |
| Linoleoyl [CH3-(CH2)4-CH = CH-CH2-CH = CH-(CH2)7-CO-, all cis] | D,Q | D,Q | D,Q | NF | Tortoriello et al. (2013) |
| Leishman et al. (2016) | |||||
| Long et al. (2016) | |||||
| α-Linolenoyl [CH3-CH2-(CH = CH-CH2)3-(CH2)6-CO-, all cis] | NF | D,Q | NF | NF | Liu et al. (2017) |
| Berman et al. (2020) | |||||
| Arachidoyl [CH3-(CH2)18-CO-] | D,Q | NF | NF | NF | Long et al. (2016) |
| Arachidonoyl [CH3-(CH2)4-(CH = CH-CH2)4-(CH2)2-CO-, all cis] | D,Q | D,Q | D,Q | D | Tan et al. (2010) |
| Leishman et al. (2016) | |||||
| Long et al. (2016) | |||||
| Borras et al. (2017) | |||||
| Berman et al. (2020) | |||||
| Eicosapentaenoyl [CH3-CH2-(CH = CH-CH2)5-(CH2)2-CO-, all cis] | D,Q | NF | NF | NF | Long et al. (2016) |
| Behenoyl [CH3-(CH2)20-CO-] | NF | NF | NF | NF | |
| Erucoyl [CH3-(CH2)7-CH = CH-(CH2)11-CO-, cis] | NF | NF | NF | NF | |
| Docosahexaenoyl [CH3-CH2-(CH = CH-CH2)6-CH2-CO-, all cis] | D,Q | D,Q | D | D | Tan et al. (2010) |
| Leishman et al. (2016) | |||||
| Long et al. (2016) | |||||
| Lignoceroyl [CH3-(CH2)22-CO-] | NF | NF | NF | NF | |
| Nervonoyl [CH3-(CH2)7-CH = CH-(CH2)13-CO-, cis] | NF | NF | NF | NF | |
a
D, detected, Q = quantified, and NF, nothing found.