From supramolecular chemistry to the nucleosome: studies in biomolecular recognition

• Marcey L. Waters

Beilstein J. Org. Chem. 2016, 12, 1863–1869, doi:10.3762/bjoc.12.175

• significant impact on how I run my own group. A turn to bioorganic chemistry An interesting thing happened while I was in graduate school. I found myself reading papers in a relatively young field: supramolecular chemistry. This interest did not simply spring forth on its own, however; the seeds were planted

Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides

• Andrew W. Truman

Beilstein J. Org. Chem. 2016, 12, 1250–1268, doi:10.3762/bjoc.12.120

• macrocyclase is found in the biosynthesis of the 14-residue sunflower trypsin inhibitor 1 (SFTI-1, Figure 8C), where asparaginyl endopeptidase (AEP) employs a catalytic triad of Asn, His and Cys to catalyse both proteolysis and cyclisation [105][114][115]. SFTI-1 is found in sunflower seeds and its precursor

• peptide, prealbumin, is processed into both SFTI-1 and albumin [115]. Evidence towards the mechanism of AEP-catalysed cyclisation was provided by an in situ assay that used the enzyme isolated from sunflower seeds [115]. This showed that the enzyme is directly responsible for cyclisation and that the

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• . viridochromogenes NRRL B-1551 spores is inhibited at pM concentrations, i.e., 200 pM (40 pg/mL). A comparable effect was also observed by applying 53 and 54 to seeds, however, only at much higher concentrations. Germination of Lepidium sativum (garden cress) seeds was clearly retarded. An additional in vitro effect

• plant pathogenic fungus Hymenoscyphus pseudoalbidus, which inhibited germination of Fraxinus excelsior (European ash) seeds [60]. In contrast, 3-methyl-2H-furo[2,3-c]pyran-2-one, a component of smoke derived from burning plant material, promotes seed germination [61]. Recently, a further regulatory

An integrated photocatalytic/enzymatic system for the reduction of CO₂ to methanol in bioglycerol–water

• Michele Aresta,
• Angela Dibenedetto,
• Tomasz Baran,
• Antonella Angelini,
• Przemysław Łabuz and
• Wojciech Macyk

Beilstein J. Org. Chem. 2014, 10, 2556–2565, doi:10.3762/bjoc.10.267

• , and the in situ photocatalytic reduction of NAD+ to NADH under visible-light irradiation, using semiconductors in water/bioglycerol mixtures. Bioglycerol is being produced in increasing volumes for bio-diesel production from oleaginous seeds. New applications for this product are being investigated [7

Autonomous assembly of synthetic oligonucleotides built from an expanded DNA alphabet. Total synthesis of a gene encoding kanamycin resistance

• Kristen K. Merritt,
• Kevin M. Bradley,
• Daniel Hutter,
• Mariko F. Matsuura,
• Diane J. Rowold and
• Steven A. Benner

Beilstein J. Org. Chem. 2014, 10, 2348–2360, doi:10.3762/bjoc.10.245

• . Each set of fragments was designed by OligArch with only one goal in mind: to give autonomous assembly the best chance of success. To this end, OligArch used three different “seeds” to initiate the fragment design [21]. The fragments were designed to have nearly identical lengths (50–52 nts) and 15–17

Biosynthesis of rare hexoses using microorganisms and related enzymes

• Zijie Li,
• Yahui Gao,
• Hideki Nakanishi,
• Xiaodong Gao and
• Li Cai

Beilstein J. Org. Chem. 2013, 9, 2434–2445, doi:10.3762/bjoc.9.281

• sanctum seeds) and investigated their synthetic application for L-glucose production from D-sorbitol (Scheme 13) [83][84]. Catalase could degrade the hydrogen peroxide byproduct and increase the conversion by removing the inhibition effect of hydrogen peroxide toward galactose oxidase and regenerating

Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties

• Catalin V. Maftei,
• Elena Fodor,
• Peter G. Jones,
• M. Heiko Franz,
• Gerhard Kelter,
• Heiner Fiebig and
• Ion Neda

Beilstein J. Org. Chem. 2013, 9, 2202–2215, doi:10.3762/bjoc.9.259

• oxadiazole core is quisqualic acid (Figure 1). This metabolite was obtained from the seeds of Quisqualis indica and Q. fructus [5][6] and is a strong agonist for AMPA (α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid) receptors and group I metabotropic glutamate receptors [7]. Furthermore, 1,2,4

Simple and rapid hydrogenation of p-nitrophenol with aqueous formic acid in catalytic flow reactors

• Rahat Javaid,
• Shin-ichiro Kawasaki,
• Akira Suzuki and
• Toshishige M. Suzuki

Beilstein J. Org. Chem. 2013, 9, 1156–1163, doi:10.3762/bjoc.9.129

• suitable for Pd plating, also acts as a barrier to prevent intermetallic diffusion of Ti and the metal catalyst. The TiO2 surface was activated with Pd seeds before electroless plating. Plating of Pd was then conducted according to the procedure described in previous reports [10][11][12]. By 5 h plating at

High-affinity multivalent wheat germ agglutinin ligands by one-pot click reaction

• Henning S. G. Beckmann,
• Heiko M. Möller and
• Valentin Wittmann

Beilstein J. Org. Chem. 2012, 8, 819–826, doi:10.3762/bjoc.8.91

• ][29][30][31][32][33][34][35][36] or from screening of combinatorial libraries [37][38] have been reported. WGA is a 36 kDa plant lectin composed of two identical glycine- and cysteine-rich subunits [39] and is enriched in the seeds of Triticum vulgaris. It is specific for terminal N-acetylneuraminic

Acid- mediated reactions under microfluidic conditions: A new strategy for practical synthesis of biofunctional natural products

• Katsunori Tanaka and
• Koichi Fukase

Beilstein J. Org. Chem. 2009, 5, No. 40, doi:10.3762/bjoc.5.40

• Japan Society for the Promotion of Science, Collaborative Development of Innovative Seeds from Japan Science and Technology Agency (JST), NEDO (project ID: 07A01014a), Research Grants from Yamada Science Foundation as well as Molecular Imaging Research Program, Grants-in-Aid for Scientific Research from

Recent progress on the total synthesis of acetogenins from Annonaceae

• Nianguang Li,
• Zhihao Shi,
• Yuping Tang,
• Jianwei Chen and
• Xiang Li

Beilstein J. Org. Chem. 2008, 4, No. 48, doi:10.3762/bjoc.4.48

• ) was originally isolated [21] from the seeds of Annona muricata in 1991. Its absolute stereochemistry except for the C-8′ position was deduced by applying Mosher’s new methodology to the monotetrahydrofuranyl ACGs such as reticulatacin [22] and by a total synthesis of (8′RS)-corossoline by Wu’s group

• was isolated from seeds of Annona squamosa and obtained as an amorphous solid, [α]D +23.8 (c 0.4, CH2Cl2) [27]. It was characterized spectroscopically, and the relative configuration of the central THF ring was assigned as being threo-trans-erythro (C16R,C19R). But the configurations at C-4 and C-10

• solamin Solamin (57), a cytotoxic mono-tetrahydrofuranic γ-lactone acetogenin isolated from Annona muricata seeds in 1991 [38], was synthesized by Kitahara’s group in 1999 [39] through a direct coupling reaction (Scheme 8). The mono-THF unit 58, which was prepared from D-glutamic acid, was treated with