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      Metabolomic and transcriptomic data on major metabolic/biosynthetic pathways in workers and soldiers of the termite Prorhinotermes simplex (Isoptera: Rhinotermitidae) and chemical synthesis of intermediates of defensive ( E)-nitropentadec-1-ene biosynthesis

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          Abstract

          Production of nitro compounds has only seldom been recorded in arthropods. The aliphatic nitroalkene ( E)-nitropentadec-1-ene ( NPD), identified in soldiers of the termite genus Prorhinotermes, was the first case documented in insects in early seventies. Yet, the biosynthetic origin of NPD has long remained unknown. We previously proposed that N PD arises through the condensation of amino acids glycine and/or l-serine with tetradecanoic acid along a biosynthetic pathway analogous to the formation of sphingolipids. Here, we provide a metabolomics and transcriptomic data of the Prorhinotermes simplex termite workers and soldiers. Data are related to NPD biosynthesis in P. simplex soldiers. Original metabolomics data were deposited in MetaboLights metabolomics database and are become publicly available after publishing the original article. Additionally, chemical synthesis of biosynthetic intermediates of NPD in nonlabeled and stable labeled forms are reported. Data extend our poor knowledge of arthropod metabolome and transcriptome and would be useful for comparative study in termites or other arthropods. The data were used for de-replication of NPD biosynthesis and published separately (Jirošová et al., 2017) [1].

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          A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs.

          Sphingosine, sphinganines and phytosphingosines and their analogs were synthesized by an aldol condensation between an iminoglycinate bearing a (+)-(1R,2R,5R)-2-hydroxy-3-pinanone group as chiral auxiliary and an appropriate aldehyde. All condensations proceeded with excellent enantioselectivity to generate the (2S,3R)-D-erythro structures in good yields.
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            Co-option of the sphingolipid metabolism for the production of nitroalkene defensive chemicals in termite soldiers

            The aliphatic nitroalkene (E)-1-nitropentadec-1-ene (NPD), reported in early seventies in soldiers of the termite genus Prorhinotermes, was the first documented nitro compound produced by insects. Yet, its biosynthetic origin has long remained unknown. Here, we investigated in detail the biosynthesis of NPD in P. simplex soldiers. First, we track the dynamics in major metabolic pathways during soldier ontogeny, with emphasis on likely NPD precursors and intermediates. Second, we propose a hypothesis of NPD formation and verify its individual steps using in vivo incubations of putative precursors and intermediates. Third, we use a de novo assembled RNA-Seq profiles of workers and soldiers to identify putative enzymes underlying NPD formation. And fourth, we describe the caste- and age-specific expression dynamics of candidate initial genes of the proposed biosynthetic pathway. Our observations provide a strong support to the following biosynthetic scenario of NPD formation, representing an analogy of the sphingolipid pathway starting with the condensation of tetradecanoic acid with l-serine and leading to the formation of a C16 sphinganine. The C16 sphinganine is then oxidized at the terminal carbon to give rise to 2-amino-3-hydroxyhexadecanoic acid, further oxidized to 2-amino-3-oxohexadecanoic acid. Subsequent decarboxylation yields 1-aminopentadecan-2-one, which then proceeds through six-electron oxidation of the amino moiety to give rise to 1-nitropentadecan-2-one. Keto group reduction and hydroxyl moiety elimination lead to NPD. The proposed biosynthetic sequence has been constructed from age-related quantitative dynamics of individual intermediates and confirmed by the detection of labeled products downstream of the administered labeled intermediates. Comparative RNA-Seq analyses followed by qRT-PCR validation identified orthologs of serine palmitoyltransferase and 3-ketodihydrosphingosine reductase genes as highly expressed in the NPD production site, i.e. the frontal gland of soldiers. A dramatic onset of expression of the two genes in the first days of soldier's life coincides with the start of NPD biosynthesis, giving further support to the proposed biosynthetic hypothesis.
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              Amino-acids and peptides. XXIX. New efficient asymmetric synthesis of alpha-amino-acid derivatives with recycle of a chiral reagent asymmetric alkylation of a chiral schiff-base from glycine

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                Author and article information

                Contributors
                Journal
                Data Brief
                Data Brief
                Data in Brief
                Elsevier
                2352-3409
                02 May 2018
                June 2018
                02 May 2018
                : 18
                : 1614-1627
                Affiliations
                [a ]The Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo n. 2, 166 10 Prague, Czech Republic
                [b ]Czech University of Life Sciences Prague, Faculty of Forestry and Wood Sciences, Kamýcká 961/129, 165 00 Praha-Suchdol, Czech Republic
                [c ]Max-Planck Institute for Chemical Ecology, Hans-Knöll-Str. 8, 07745 Jena, Germany
                [d ]Biology Centre CAS, Branišovská 31, CZ-37005 České Budějovice, Czech Republic
                [e ]Faculty of Science, Charles University in Prague, Viničná 7, 128 44 Prague, Czech Republic
                Author notes
                [* ]Corresponding author at: Max-Planck Institute for Chemical Ecology, Hans-Knöll-Str. 8, 07745 Jena, Germany. svatos@ 123456ice.mpg.de
                Article
                S2352-3409(18)30403-7
                10.1016/j.dib.2018.04.052
                5997979
                bdbfc5c8-7a9d-404e-994c-4530c234a476
                © 2018 Published by Elsevier Inc.

                This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).

                History
                : 21 January 2017
                : 7 March 2018
                : 13 April 2018
                Categories
                Agricultural and Biological Sciences

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