A Streptomyces P450 enzyme dimerizes isoflavones from plants

• Run-Zhou Liu,
• Shanchong Chen and
• Lihan Zhang

Beilstein J. Org. Chem. 2022, 18, 1107–1115, doi:10.3762/bjoc.18.113

• range of m/z 50–1600. For MS–MS analysis, the collision-induced dissociation (CID) energy was set to 15–40 eV or 30–50 eV depending on the compounds. The HPLC–UV analysis of the chiral separation was conducted with a CHIRALCEL OX-3R column (150 mm × 4.6 mm, 3 μm, DAICEL) with isocratic 35% B at a flow

Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa

• Shou-Mao Shen,
• Qing Yang,
• Yi Zang,
• Jia Li,
• Xueting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 916–925, doi:10.3762/bjoc.18.91

• anti-inflammatory activity by the inhibition of LPS-induced TNF-α and CCL2 release in RAW 264.7 macrophages. Keywords: Acanthella cavernosa; anti-inflammatory; biosynthetic pathway; chiral separation; marine sponge; sesquiterpenoid; Introduction Marine sponges of the genus Acanthella (class

• with five related known ones [2, 3, (−)-4, 6, and 7] (Figure 1), were obtained. Herein, we report the isolation, chiral separation of racemic mixtures of 4 and 5, structural elucidation, plausible biosynthetic pathway, and biological evaluation of these isolated compounds. Results and Discussion By the

• (J in Hz) and 13C NMR data of compounds (+)-1, 4, and 5. Supporting Information Supporting Information File 160: HPLC chromatograms of 4 and 5, chiral separation of 4 and 5, X-ray crystallographic data for 2, spectra of compounds (+)-1, 4 and 5, TDDFT-ECD calculation of compound (+)-1

Circularly polarized luminescent systems fabricated by Tröger's base derivatives through two different strategies

• Cheng Qian,
• Yuan Chen,
• Qian Zhao,
• Ming Cheng,
• Chen Lin,
• Juli Jiang and
• Leyong Wang

Beilstein J. Org. Chem. 2021, 17, 52–57, doi:10.3762/bjoc.17.6

• -TBPP and S2N-TBPP are +0.0021, and −0.0025, repectively (Figure 1b), which is larger than many small organic molecules [25]. In order to avoid a tedious chiral separation of rac-TBPP, we tried to construct the CPL-active material by co-assembling the achiral fluorophore rac-TBPP with a chiral gelator

Novel macrocycles – and old ones doing new tricks

• Wei Jiang and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2019, 15, 1838–1839, doi:10.3762/bjoc.15.178

• diversified. They are not only tools for studying molecular recognition and molecular machines, but are also key components for sensing, supramolecular catalysis, (chiral) separation, drug delivery, or smart materials. Many new macrocycles have recently been reported, with pillararenes being one of the most

Synthesis, enantioseparation and photophysical properties of planar-chiral pillar[5]arene derivatives bearing fluorophore fragments

• Guojuan Li,
• Chunying Fan,
• Guo Cheng,
• Wanhua Wu and
• Cheng Yang

Beilstein J. Org. Chem. 2019, 15, 1601–1611, doi:10.3762/bjoc.15.164

• the chiral separation of the Sp and Rp enantiomers [25]. Also installing bulky substituents onto only one phenolic ring was found to be effective to inhibit the rotation of the units [27][28][29]. Pillar[5]arene itself shows only moderate absorption and weak fluorescence in the UV region, and the

Determination of the absolute stereostructure of a cyclic azobenzene from the crystal structure of the precursor containing a heavy element

• Reji Thomas and
• Nobuyuki Tamaoki

Beilstein J. Org. Chem. 2016, 12, 2211–2215, doi:10.3762/bjoc.12.212

• ][17][18][19][20][21][22] and magnetic properties [23][24][25]. Hence, the chiral separation and the determination of absolute stereostructure are important aspects of stereochemistry for the complete understanding of the role of chiral structures in various physical and biological functions. Until

Supramolecular structures based on regioisomers of cinnamyl-α-cyclodextrins – new media for capillary separation techniques

• Gabor Benkovics,
• Ondrej Hodek,
• Martina Havlikova,
• Zuzana Bosakova,
• Pavel Coufal,
• Milo Malanga,
• Eva Fenyvesi,
• Andras Darcsi,
• Szabolcs Beni and
• Jindrich Jindrich

Beilstein J. Org. Chem. 2016, 12, 97–109, doi:10.3762/bjoc.12.11

• separation media in separation science remained an unexplored area [2]. The recent work focused on the preparation of supramolecular structures based on cyclodextrin (CD) [3] derivatives and on their application as chiral separation environment in capillary separation techniques. CDs are widely used in

Chiroptical properties of 1,3-diphenylallene-anchored tetrathiafulvalene and its polymer synthesis

• Masashi Hasegawa,
• Junta Endo,
• Seiya Iwata,
• Toshiaki Shimasaki and
• Yasuhiro Mazaki

Beilstein J. Org. Chem. 2015, 11, 972–979, doi:10.3762/bjoc.11.109

• (9) with a TTF-zinc intermediate (Scheme 1). Previously, 1,3-bis(2-bromophenyl)allene derivatives were reported by Ready et al. as a precursor of an asymmetric catalyst [18]. To obtain the chiral 1,3-bis(4-bromophenyl)allene (8) in a larger scale, we modified the synthesis and the chiral separation

Synthesis of modified cyclic and acyclic dextrins and comparison of their complexation ability

• Kata Tuza,
• László Jicsinszky,
• Tamás Sohajda,
• István Puskás and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 2836–2843, doi:10.3762/bjoc.10.301

• derivatives behaved similarly, although the enantiorecognition properties frequently differed. For example, the enantiomers of chrysanthemic acid were only recognized by HP-β-CD whereas the only host resulting in a partial chiral separation of chlorpheniramine enantiomers was HP-G6 (Figure 2, fifth and first

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

• Gijs Koopmanschap,
• Eelco Ruijter and
• Romano V.A. Orru

Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50

• , thioacetic acid and 4-methoxy-phenylethylamine (also as chiral auxiliary) provided the corresponding Ugi product 138 in 60% yield (dr 1:1). Chiral separation and deprotection in TFA resulted in compound 139 in 70% yield, after which saponification followed by an amide coupling with tryptamine and CDI

Elucidation of the regio- and chemoselectivity of enzymatic allylic oxidations with Pleurotus sapidus – conversion of selected spirocyclic terpenoids and computational analysis

• Verena Weidmann,
• Mathias Schaffrath,
• Holger Zorn,
• Julia Rehbein and
• Wolfgang Maison

Beilstein J. Org. Chem. 2013, 9, 2233–2241, doi:10.3762/bjoc.9.262

• Pleurotus sapidus. This ‘’mushroom catalysis’’ is operationally simple and allows the conversion of various unsaturated spirocyclic terpenoids. A number of new spirocyclic enones have thus been obtained with good regio- and chemoselectivity and chiral separation protocols for enantiomeric mixtures have been

• developed. The oxidations follow a radical mechanism and the regioselectivity of the reaction is mainly determined by bond-dissociation energies of the available allylic CH-bonds and steric accessibility of the oxidation site. Keywords: allylic oxidation; CH-activation; chiral separation; enones; flavors

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

• conditions for chiral separation of amines and amino alcohols [180]. The azophenolic crown ether was a versatile and a highly enantioselective host for their chiral separation by reactive extraction. Transport from a basic aqueous solution of the racemic mixture in CH2Cl2 and toluene was followed by UV–vis

Asymmetric reactions in continuous flow

• Xiao Yin Mak,
• Paola Laurino and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2009, 5, No. 19, doi:10.3762/bjoc.5.19

• -mL continuous flow reactor when 221 g of alcohol 48 were processed, providing consistent results over a period of 3 days. An interesting example of a chiral separation using a cross-linked polymeric acylase aggregate immobilized in a microreactor was reported by Maeda and coworkers [57]. Taking