Chirped-pulsed FTMW spectra of valeric acid, 5-aminovaleric acid, and δ-valerolactam: A study of amino acid mimics in the gas phase

Bird, Ryan G.; Vaquero-Vara, Vanesa; Zaleski, Daniel P.; Pate, Brooks H.; Pratt, David W.

doi:10.1016/j.jms.2012.06.017

Cited by 15 publications

(13 citation statements)

References 19 publications

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“…S2A and S6). This is consistent with the previously reported LysOx-catalyzed generation of 5-aminovaleric acid from L-Lys (Kusakabe et al, 1980;Pukin et al, 2010), since 5-aminovaleric acid is able to spontaneously cyclize to valerolactam (Bird et al, 2012). The fragmentation patterns of the isotope-labeled valerolactam derivatives also suggest that, like 2,3-DP, valerolactam is produced from LysOx by abstraction of the a-NH 2 group of Lys (Supplemental Fig.…”

Section: Resultssupporting

confidence: 91%

Biochemical Principles and Functional Aspects of Pipecolic Acid Biosynthesis in Plant Immunity

et al. 2017

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The nonprotein amino acid pipecolic acid (Pip) regulates plant systemic acquired resistance and basal immunity to bacterial pathogen infection. In Arabidopsis (Arabidopsis thaliana), the lysine (Lys) aminotransferase AGD2-LIKE DEFENSE RESPONSE PROTEIN1 (ALD1) mediates the pathogen-induced accumulation of Pip in inoculated and distal leaf tissue. Here, we show that ALD1 transfers the a-amino group of L-Lys to acceptor oxoacids. Combined mass spectrometric and infrared spectroscopic analyses of in vitro assays and plant extracts indicate that the final product of the ALD1-catalyzed reaction is enaminic 2,3-dehydropipecolic acid (DP), whose formation involves consecutive transamination, cyclization, and isomerization steps. Besides L-Lys, recombinant ALD1 transaminates L-methionine, L-leucine, diaminopimelate, and several other amino acids to generate oxoacids or derived products in vitro. However, detailed in planta analyses suggest that the biosynthesis of 2,3-DP from L-Lys is the major in vivo function of ALD1. Since ald1 mutant plants are able to convert exogenous 2,3-DP into Pip, their Pip deficiency relies on the inability to form the 2,3-DP intermediate. The Arabidopsis reductase ornithine cyclodeaminase/m-crystallin, alias SYSTEMIC ACQUIRED RESISTANCE-DEFICIENT4 (SARD4), converts ALD1-generated 2,3-DP into Pip in vitro. SARD4 significantly contributes to the production of Pip in pathogen-inoculated leaves but is not the exclusive reducing enzyme involved in Pip biosynthesis. Functional SARD4 is required for proper basal immunity to the bacterial pathogen Pseudomonas syringae. Although SARD4 knockout plants show greatly reduced accumulation of Pip in leaves distal to P. syringae inoculation, they display a considerable systemic acquired resistance response. This suggests a triggering function of locally accumulating Pip for systemic resistance induction.

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Section: Resultssupporting

confidence: 91%

Biochemical Principles and Functional Aspects of Pipecolic Acid Biosynthesis in Plant Immunity

et al. 2017

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“…[24] Finally, the n-p* interaction is considered responsible for the thermal conversion of 5aminovaleric acid to d-valerolactam. [25] This represents another interesting experimental evidence on the investigation of weak interaction, provided by rotational spectroscopy.…”

Section: Methodsmentioning

confidence: 89%

Lone‐Pair⋅⋅⋅π Interaction: A Rotational Study of the Chlorotrifluoroethylene–Water Adduct

et al. 2013

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“…[24] Finally, the n-p* interaction is considered responsible for the thermal conversion of 5-aminovaleric acid to d-valerolactam. [25] This represents another interesting experimental evidence on the investigation of weak interaction, provided by rotational spectroscopy.…”

Section: Methodsmentioning

confidence: 89%

Lone‐Pair⋅⋅⋅π Interaction: A Rotational Study of the Chlorotrifluoroethylene–Water Adduct

et al. 2013

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Chirped-pulsed FTMW spectra of valeric acid, 5-aminovaleric acid, and δ-valerolactam: A study of amino acid mimics in the gas phase

Cited by 15 publications

References 19 publications

Biochemical Principles and Functional Aspects of Pipecolic Acid Biosynthesis in Plant Immunity

Biochemical Principles and Functional Aspects of Pipecolic Acid Biosynthesis in Plant Immunity

Lone‐Pair⋅⋅⋅π Interaction: A Rotational Study of the Chlorotrifluoroethylene–Water Adduct

Lone‐Pair⋅⋅⋅π Interaction: A Rotational Study of the Chlorotrifluoroethylene–Water Adduct

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