New variochelins from soil-isolated Variovorax sp. H002

• Jabal Rahmat Haedar,
• Aya Yoshimura and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2024, 20, 692–700, doi:10.3762/bjoc.20.63

• for 1 h with 10 mg/mL lysozyme. After 10% SDS was added to the tube, the mixture was incubated at room temperature, 60 °C, and then 0 °C, for 5 min durations. AcOK (5 M) and phenol/CHCl3/isoamyl alcohol (25:24:1) were then added, and the resulting solution was gently mixed by inversion and centrifuged

A myo-inositol dehydrogenase involved in aminocyclitol biosynthesis of hygromycin A

• Michael O. Akintubosun and
• Melanie A. Higgins

Beilstein J. Org. Chem. 2024, 20, 589–596, doi:10.3762/bjoc.20.51

• , the pellet was resuspended in 40 mL of sucrose solution (25% sucrose, 50 mM Tris pH 8) using continuous stirring. Then, 10 mg of lysozyme (Bio Basic) was added and stirred at room temperature for 10 min, followed by the addition of 80 mL deoxycholate solution (1% deoxycholate, 1% Triton X-100, 100 mM

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

• such as β-lactoglobulin, lysozyme or crystallins is based on a complex interplay of various attractive forces such as hydrogen bonding, electrostatic as well as π–π interactions and hydrophobic effects [302][304][305] Several studies show that in the

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• glycosidic bond [216]. Various enzymes have been successfully employed, including β-N-acetyl-hexosaminidase [242], lysozyme (Scheme 9) [243], and endochitinase [244][245][246]. With these approaches, structures with a DP up to 13 could be accessed. Genetically engineered transglycosylating hydrolases were

NMR Spectroscopy of supramolecular chemistry on protein surfaces

• Peter Bayer,
• Anja Matena and
• Christine Beuck

Beilstein J. Org. Chem. 2020, 16, 2505–2522, doi:10.3762/bjoc.16.203

• ]arene to dimethyl-lysine (KMe2) residues in the model protein lysozyme [22]. The preferred calixarene binding site was identified by tracking the signals of the lysine methyl groups, which can easily be identified in a 1H,13C-HSQC spectrum in the spectral region of 2–3 ppm for 1H and 40–45 ppm in the

Olefin metathesis catalysts embedded in β-barrel proteins: creating artificial metalloproteins for olefin metathesis

• Daniel F. Sauer,
• Johannes Schiffels,
• Takashi Hayashi,
• Ulrich Schwaneberg and
• Jun Okuda

Beilstein J. Org. Chem. 2018, 14, 2861–2871, doi:10.3762/bjoc.14.265

• catalyst and carbohydrate or small polyethylene glycol (PEG) groups were attached [11]. As another strategy to modify a protein surface with olefin metathesis, Isarov and Pokorski introduced a Grubbs 3rd generation catalyst on the surface of lysozyme and performed ring-opening metathesis polymerization

Investigation of the electrophilic reactivity of the biologically active marine sesquiterpenoid onchidal and model compounds

• Melissa M. Cadelis and
• Brent R. Copp

Beilstein J. Org. Chem. 2018, 14, 2229–2235, doi:10.3762/bjoc.14.197

• model protein lysozyme, forming covalent adducts and leading to protein cross-linking. These results provide preliminary evidence supporting the molecular mechanism of biological activity exhibited by onchidal. Keywords: dialdehyde; lysozyme; mollusc; onchidal; pyrrole; Introduction More than 80

• simplified n-pentyl and cyclohexylmethyl model compounds towards thiol and amine nucleophiles as well as their reactivity towards a model protein target, lysozyme. Results and Discussion Preliminary studies of the reactivity of onchidal (6) towards 1-pentanethiol or 1-pentylamine were undertaken in CDCl3

• , Figure 4), while enol esters 13 and 17 gave 29 and 31 (7% and 5% yields), respectively, upon reaction with the amine nucleophile. We next investigated the reactivity of onchidal (6) and analogues 11–13 and 15–17 towards the lysine-rich model protein lysozyme. Previous studies have reported hen egg white

Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor

• Morten M. C. H. van Schie,
• Tiago Pedroso de Almeida,
• Gabriele Laudadio,
• Florian Tieves,
• Elena Fernández-Fueyo,
• Timothy Noël,
• Isabel W. C. E. Arends and
• Frank Hollmann

Beilstein J. Org. Chem. 2018, 14, 697–703, doi:10.3762/bjoc.14.58

• volume of 40 mL 50 mM Tris/HCl buffer, pH 8.0, containing 10 mM EDTA and 5 mM dithiothreitol (DTT). Refolding The re-suspended cells were disrupted by incubation with 2 mg mL−1 lysozyme for 1 h at 4 °C. Afterwards, 0.1 mg mL−1 DNase, 1 mM MgCl2 and 0.1 mM PMSF were added followed by sonication. The

Superstructures with cyclodextrins: Chemistry and applications IV

• Gerhard Wenz

Beilstein J. Org. Chem. 2017, 13, 2157–2159, doi:10.3762/bjoc.13.215

• insulin and lysozyme were also conjugated to the guest adamantane. The complexation of these conjugates by pegylated β-CD gives rise to superstructures which provide slow release and maintain full biological activity [21]. Significant progress was also achieved in the field of CD rotaxanes. A [3]-rotaxane

G-Protein coupled receptors: answers from simulations

• Timothy Clark

Beilstein J. Org. Chem. 2017, 13, 1071–1078, doi:10.3762/bjoc.13.106

• , polar fragment such as the T4 lysozyme [10][11] or other suitable protein fragments [12]. Other techniques used to obtain GPCR crystals include mutations to enhance the thermal stability [13], solubilization with custom detergents [14] or in conjunction with high-affinity ligands, which promote one

Synthesis and enzymatic ketonization of the 5-(halo)-2-hydroxymuconates and 5-(halo)-2-hydroxy-2,4-pentadienoates

• Tyler M. M. Stack,
• William H. Johnson Jr. and
• Christian P. Whitman

Beilstein J. Org. Chem. 2017, 13, 1022–1031, doi:10.3762/bjoc.13.101

• -Protean II gel electrophoresis apparatus. Purification of 4-OT from L. cholodnii SP-6 In a typical procedure, frozen cells (25 g) were thawed on ice and suspended in 120 mL of 20 mM NaH2PO4 buffer (pH 7.3). Lysozyme was added to the cell suspension to a final concentration of 5 mg/mL and the resulting

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• carboxymethyl-β-CD (CM-β-CD) in the electrophoretic medium (aqueous buffer solution, pH 2.5) enhanced the separation in capillary zone electrophoresis (raw fused-silica) of standard proteins such as α-chymotrypsinogen A, cytochrome c, lysozyme and ribonuclease A [90]. The obtained results proved that the

• group of Yamamoto studied the effect of β-, γ-, G1-β-, and Me-α-CD on the thermal stability of an aqueous buffered solution of chicken egg white lysozyme by circular dichroism and fluorescence spectroscopy [91]. The thermal stability is significantly lowered in the presence of β-, γ-, and G1-β-CD

• whereas the opposite is true for the Me-α-CD. It should be noted that the thermal stability reduction is very important for G1-β-CD. Based on fluorescence spectroscopy, the authors suggested that CDs include the side chains of tryptophan (Trp) residues of lysozyme within their internal cavities to

Highly stable and reusable immobilized formate dehydrogenases: Promising biocatalysts for in situ regeneration of NADH

• Barış Binay,
• Dilek Alagöz,
• Deniz Yildirim,
• Ayhan Çelik and
• S. Seyhan Tükel

Beilstein J. Org. Chem. 2016, 12, 271–277, doi:10.3762/bjoc.12.29

• further lysed by adding lysozyme. Then the lysate was filtered through a 0.45 μm filter. The filtered samples were loaded to a His-trap column after equilibration with 5 mL of the ice-cold buffer. Then the column was washed with 5 mL of the same buffer. FDH was eluted with a series of elution buffers: 3

Preparation and evaluation of cyclodextrin polypseudorotaxane with PEGylated liposome as a sustained release drug carrier

• Kayoko Hayashida,
• Taishi Higashi,
• Daichi Kono,
• Keiichi Motoyama,
• Koki Wada and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2014, 10, 2756–2764, doi:10.3762/bjoc.10.292

• ][22]. Also, α- and γ-CDs formed PPRXs with PEGylated proteins and provided sustained release profiles of PEGylated insulin and PEGylated lysozyme in vitro and in vivo [10][23][24][25]. Furthermore, α- and γ-CDs PPRXs with PEGylated PAMAM dendrimer and α-CD-appended PEGylated PAMAM dendrimer were

Why a diaminopyrrolic tripodal receptor binds mannosides in acetonitrile but not in water?

• Diogo Vila-Viçosa,
• Oscar Francesconi and
• Miguel Machuqueiro

Beilstein J. Org. Chem. 2014, 10, 1513–1523, doi:10.3762/bjoc.10.156

• , using MM/MD simulations, showed that the major contribution to the binding energy between both glucose and galactose to a proteic receptor, came from hydrogen bonds [38]. Moreover, Lerbret et al, suggested that hydrogen bonds are strongly related with the influence of sugar molecules in lysozyme

True and masked three-coordinate T-shaped platinum(II) intermediates

• Manuel A. Ortuño,
• Salvador Conejero and
• Agustí Lledós

Beilstein J. Org. Chem. 2013, 9, 1352–1382, doi:10.3762/bjoc.9.153

• pyridine S19a and acetonitrile S19b,c adducts [91]. The relevance of solvent-stabilized T-shaped Pt(II) complexes extends beyond the organometallic field. Their presence in cisplatin–protein adducts has also been proposed concerning the bovine Cu, Zn superoxide dismutase [92] and the hen egg white lysozyme

• water molecule. Indeed, quantum mechanics/molecular mechanics (QM/MM) calculations on the cisplatin–hen egg white lysozyme adduct confirmed the facile inclusion of a solvent water molecule in the first coordination shell of the platinum complex (Figure 13) [94]. NMR coupling constants to 195Pt as

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• carried out, showing a prolonged release of albumin from the two swellable β-CD-nanosponges over a period of 24 h. The encapsulation of albumin and its prolonged release was also obtained with carbonate nanosponges (unpublished data). NS10 and NS11 were recently used to incorporate lysozyme and showed a

• high loading capacity. The encapsulation efficiency and loading percentages were 89% and 17% for NS10 and 96% and 19.6 for NS11. These lysozyme-loaded nanosponges released the enzyme at a pH-dependent rate with prolonged kinetics, whilst maintaining its biological activity [44]. Oral delivery systems

Similarity analysis, synthesis, and bioassay of antibacterial cyclic peptidomimetics

• Workalemahu M. Berhanu,
• Mohamed A. Ibrahim,
• Girinath G. Pillai,
• Alexander A. Oliferenko,
• Levan Khelashvili,
• Farukh Jabeen,
• Bushra Mirza,
• Farzana Latif Ansari,
• Ihsan ul-Haq,
• Said A. El-Feky and
• Alan R. Katritzky

Beilstein J. Org. Chem. 2012, 8, 1146–1160, doi:10.3762/bjoc.8.128

• associated with zinc cations and/or surfactants [30][31][32]. Anionic peptides bind with lysozyme, an important cationic hydrolytic enzyme. It is believed that the lysozyme opens the cell wall, “allowing a small anionic peptide to penetrate”. Topical administration of such anionic peptides is possible, for

Mutational analysis of a phenazine biosynthetic gene cluster in Streptomyces anulatus 9663

• Orwah Saleh,
• Katrin Flinspach,
• Lucia Westrich,
• Andreas Kulik,
• Bertolt Gust,
• Hans-Peter Fiedler and
• Lutz Heide

Beilstein J. Org. Chem. 2012, 8, 501–513, doi:10.3762/bjoc.8.57

• . Lysozyme was from Boehringer Ingelheim, Heidelberg, Germany. Genetic procedures Standard methods for DNA isolation and manipulation were performed as described by Kieser et al. [36] and Sambrook et al. [39]. DNA fragments were isolated from agarose gels by using a PCR purification kit (Amersham Biosciences

• ). Genomic DNA was isolated by lysozyme treatment and phenol/chloroform extraction as described by Kieser et al. [36]. The construction, screening and heterologous expression of the phenazine biosynthetic gene cluster from S. anulatus was previously described [11]. Construction of cosmids ppzOS10, ppzOS11

• a further 10 h at 20 °C and harvested. Then, 30 mL of lysis buffer (50 mM Tris-HCl, pH 8.0, 1 M NaCl, 10% glycerol, 10 mM β-mercaptoethanol, 20 mM imidazole, 0.5 mg·mL−1 lysozyme, 0.5 mM phenylmethylsulfonyl fluoride) was added to the pellet (40 g). After being stirred at 4 °C for 30 min, cells were

RAFT polymers for protein recognition

• Alan F. Tominey,
• Julia Liese,
• Sun Wei,
• Klaus Kowski,
• Thomas Schrader and
• Arno Kraft

Beilstein J. Org. Chem. 2010, 6, No. 66, doi:10.3762/bjoc.6.66

• . In their elegant work, Kulkarni et al. reported the use of NIPAM-based copolymers for lysozyme recovery by affinity thermoprecipitation. These polymers contained multiple acetamido groups in a hydrophilic environment for maximum interaction with the catalytic cleft and achieved high affinities [5

• could be detected for the short version, indicating that size matters and promotes multivalent or cooperative binding. Finally, the protein series was extended to lysine-rich histone (pI 10), lysozyme (pI 9), proteinase K (pI 8) and bovine serum albumin or BSA (pI 6). Again, the strong binders B20CH15

• – admittedly much weaker – 2:1 complex. Histone association with B20CH15 is an illustrative example. The first Kd value is 16 nM, followed by very weak binding at a second site with a Kd of 1 mM. With respect to varying pI values, both RAFT polymers display little selectivity: From lysozyme (pI > 9) down to