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Chemistry – An Asian Journal

Cover image for Vol. 6 Issue 10

Special Issue: Celebrating the 10th Anniversary of Click Chemistry

October 4, 2011

Volume 6, Issue 10

Pages 2565–2847

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Focus Reviews
    8. Communications
    9. Full Papers
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      Cover Picture: (Chem. Asian J. 10/2011) (page 2565)

      Version of Record online: 28 SEP 2011 | DOI: 10.1002/asia.201190040

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      This year marks the 10th anniversary of Click Chemistry, which has rapidly become a key feature in diverse research areas ranging from organic synthesis to chemical biology and materials science. To mark this anniversary, this issue is a special issue celebrating the influence that Click Chemistry has had on the whole spectrum of chemistry. This issue, co-organized by Qian Wang and Craig Hawker, contains nine Focus Reviews and 14 original research papers.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Focus Reviews
    8. Communications
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      Inside Cover: Click to Join Peptides/Proteins Together (Chem. Asian J. 10/2011) (page 2566)

      Dr. Xuechen Li

      Version of Record online: 28 SEP 2011 | DOI: 10.1002/asia.201190041

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      Click to Ligate Copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) represents a high-yielding, chemoselective, regioselective, bio-orthogonal, and easy-to-perform reaction. In addition, the resultant triazole moiety resembles the natural peptide bond in many aspects. In the Focus Review on page 2606 ff, X. Li has reviewed and discussed the advancement of CuAAC reactions in peptide/protein ligation. The application of click chemistry in synthetic protein chemistry is still at an early stage; nevertheless it is an exciting and promising research area for explorations.

  3. Editorial

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Focus Reviews
    8. Communications
    9. Full Papers
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  4. Graphical Abstract

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    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Focus Reviews
    8. Communications
    9. Full Papers
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  5. News

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    4. Editorial
    5. Graphical Abstract
    6. News
    7. Focus Reviews
    8. Communications
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  6. Focus Reviews

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    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Focus Reviews
    8. Communications
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    1. Polymers

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      Synthesis of Terpolymers by Click Reactions (pages 2584–2591)

      Ozcan Altintas and Prof. Umit Tunca

      Version of Record online: 18 MAY 2011 | DOI: 10.1002/asia.201100138

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      Cycloadditions: Well-defined polymeric structures were easily generated through living polymerization systems, in particular, living radical polymerizations. These precursors with orthogonal functionalities were subsequently clicked with each other in a single or double (combination) click reaction (see scheme).

    2. Click Chemistry

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      Click Chemistry-Based Functionalization on Non-Oxidized Silicon Substrates (pages 2592–2605)

      Dr. Yan Li and Prof. Dr. Chengzhi Cai

      Version of Record online: 12 JUL 2011 | DOI: 10.1002/asia.201100294

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      Silicon ally: The stable Si[BOND]C-bound organic layer combined with highly reliable click chemistry serves as an efficient tool for the modification of silicon substrates (see scheme). This review covers the advances in the development of the copper-catalyzed azide–alkyne cycloaddition on non-oxidized silicon and highlights its application in the immobilization of complex biomolecules that makes it useful in the fabrication of silicon-based biomedical devices.

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      Click to Join Peptides/Proteins Together (pages 2606–2616)

      Dr. Xuechen Li

      Version of Record online: 16 AUG 2011 | DOI: 10.1002/asia.201100329

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      Click to join: The copper(I)-catalyzed azide–alkyne cycloaddition has allowed the merger of peptide chains in a “click” fashion with the generation of the peptide-bond-like triazole structure at the ligation site. It holds great potential in the non-native chemical synthesis of polypeptides and proteins.

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      Sulfonyl and Phosphoryl Azides: Going Further Beyond the Click Realm of Alkyl and Aryl Azides (pages 2618–2634)

      Seok Hwan Kim, Sae Hume Park, Ji Ho Choi and Prof. Dr. Sukbok Chang

      Version of Record online: 11 JUL 2011 | DOI: 10.1002/asia.201100340

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      Versatile middleman: Whereas alkyl or aryl azides undergo Cu-catalyzed cycloaddition with 1-alkynes to afford 1,4-triazoles in excellent yields and selectivity, the use of sulfonyl, phosphoryl, and certain acyl azides allows additional chemistry upon ring-opening of the corresponding triazole intermediates (see scheme). The ketenimine species generated in situ show amazing reactivity and can react with a range of nucleophilic coupling partners.

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      Steroid/Triterpenoid Functional Molecules based on “Click Chemistry” (pages 2636–2647)

      J. Hu, J. R. Lu and Prof.  Y. Ju

      Version of Record online: 2 SEP 2011 | DOI: 10.1002/asia.201100378

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      They're on steroids and triterpenoids! This Focus Review highlights the design and synthesis of various functional molecules based on steroid/triterpenoid units through the copper-catalyzed azide–alkyne cycloaddition (CuAAC) “click” reaction, as well as their applications in bioactivity, recognition, and assembly.

    6. Hydrogels

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      Fabrication and Functionalization of Hydrogels through “Click” Chemistry (pages 2648–2659)

      Sezin Yigit, Prof. Rana Sanyal and Prof. Amitav Sanyal

      Version of Record online: 29 AUG 2011 | DOI: 10.1002/asia.201100440

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      Chemical jigsaw puzzles! This Focus Review highlights the tremendous impact of click chemistry on the design and fabrication of functional hydrogels. The efficiency and specificity of click reactions have enabled precise ‘programming’ of assembly and disassembly of these materials by ‘snapping’ together complementary building blocks like pieces of a puzzle to create the intended functional material.

    7. Supramolecular Chemistry

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      Reactions under the Click Chemistry Philosophy Employed in Supramolecular and Mechanostereochemical Systems (pages 2660–2669)

      Albert C. Fahrenbach and Prof. J. Fraser Stoddart 

      Version of Record online: 2 SEP 2011 | DOI: 10.1002/asia.201100457

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      Click into action: The philosophy of click chemistry has taken the chemistry community by storm over the past 10 years. This Focus Reviews highlights some of the recent developments in supramolecular and mechanostereochemistry, which employ one of the click reactions depicted here in their syntheses.

    8. Triazoles

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      10 Years of Click Chemistry: Synthesis and Applications of Ferrocene-Derived Triazoles (pages 2670–2694)

      Venkataraman Ganesh, Dr. V. Sai Sudhir, Dr. Taraknath Kundu and Prof. Srinivasan Chandrasekaran

      Version of Record online: 31 AUG 2011 | DOI: 10.1002/asia.201100408

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      Focus on ferrocene: We discuss the synthesis of ferrocene–triazole and the importance of using a copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction for the conjugation of two molecular fragments. We also highlight applications of ferrocene-based click reactions in conjugate chemistry, asymmetric catalysis, medicinal chemistry, host–guest interactions, and materials chemistry (see graphic).

    9. Cycloaddition

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      Click Chemistry: 1,2,3-Triazoles as Pharmacophores (pages 2696–2718)

      Sandip G. Agalave, Dr. Suleman R. Maujan and Dr. Vandana S. Pore

      Version of Record online: 29 AUG 2011 | DOI: 10.1002/asia.201100432

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      Easy as 1,2,3: Click chemistry is used for the synthesis of 1,2,3-triazole wherein the CuI is used as catalyst to obtain 1,4-disubstituted triazole as the sole product (see scheme). This review explains the excellent use of click chemistry for the synthesis of a number of biologically important intermediates, linkers, lead molecules, and various drugs.

  7. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Focus Reviews
    8. Communications
    9. Full Papers
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    1. Mitsunobu Reaction

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      Mitsunobu Reaction of 1,2,3-NH-Triazoles: A Regio- and Stereoselective Approach to Functionalized Triazole Derivatives (pages 2720–2724)

      Wuming Yan, Tao Liao, Odbadrakh Tuguldur, Dr. Cheng Zhong, Prof. Dr. Jeffrey L. Petersen and Prof. Dr. Xiaodong Shi

      Version of Record online: 29 JUN 2011 | DOI: 10.1002/asia.201100357

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      The Mitsunobu reaction was used in the preparation of chiral triazole derivatives. The reactions gave good to excellent yields with large substrate scope. Complete stereochemistry inversion was obtained, making this strategy one practical approach for the synthesis of enantiomeric enriched triazole analogous.

    2. Fluorescence Sensors

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      A Highly Selective and Sensitive Polymer-based Fluorescence Sensor for Hg2+-Ion Detection via Click Reaction (pages 2725–2729)

      Yuanzhao Wu, Yu Dong, Junfeng Li, Xiaobo Huang, Yixiang Cheng and Chengjian Zhu

      Version of Record online: 17 AUG 2011 | DOI: 10.1002/asia.201100534

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      Mercury rising: A Highly Selective and sensitive polymer-based fluorescence sensor synthesized using click reactions affords the most-pronounced fluorescence response to Hg2+ ions.

  8. Full Papers

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    3. Inside Cover
    4. Editorial
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    6. News
    7. Focus Reviews
    8. Communications
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    1. Cell Encapsulation

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      Cytocompatible Poly(ethylene glycol)-co-polycarbonate Hydrogels Cross-Linked by Copper-Free, Strain-Promoted Click Chemistry (pages 2730–2737)

      Dr. Jianwen Xu, Tera M. Filion, Fioleda Prifti and Prof. Jie Song

      Version of Record online: 24 AUG 2011 | DOI: 10.1002/asia.201100411

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      Trapped in a gel: Cytocompatible hydrogels with various mechanical properties were prepared through copper-free, strain-promoted azide–alkyne cycloaddition under physiological conditions (see figure). Bone marrow stromal cells encapsulated in these gels exhibited higher cellular viability than those in photo-cross-linked poly(ethylene glycol) dimethacrylate.

    2. Fluorescence

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      1,3-Alternate Calix[4]arene as a Homobinuclear Ditopic Fluorescent Chemosensor for Ag+ Ions (pages 2738–2746)

      Dr. I-Ting Ho, Kuan-Chang Haung and Prof. Dr. Wen-Sheng Chung

      Version of Record online: 19 APR 2011 | DOI: 10.1002/asia.201100023

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      A ditopic fluorescent chemosensor: The selective binding of one or two equivalents of Ag+ ions with opposite fluorescence responses was accomplished by the judicious design and synthesis of chelation ligands on both sides of the 1,3-alternate calix[4]arene skeleton using click chemistry, 1,3-dipolar cycloaddition, and subsequent ring-opening procedures.

    3. DNA Modification

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      Design, Synthesis, and Polymerase-Catalyzed Incorporation of Click-Modified Boronic Acid–TTP Analogues (pages 2747–2752)

      Yunfeng Cheng, Dr. Chaofeng Dai, Hanjing Peng, Dr. Shilong Zheng, Dr. Shan Jin and Prof. Binghe Wang

      Version of Record online: 2 SEP 2011 | DOI: 10.1002/asia.201100229

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      That′s just boronic! The incorporation of boronic acid-modified nucleobases affords unique DNA properties for applications in areas that are otherwise difficult or not possible. An approach to achieve this, which is much more efficient than the previously described methods, is described. This paves the way for the preparation of a large number of boronic acid-modified thymidine triphosphates with a diverse set of structural features.

    4. Polyacetylenes

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      Ferrocene-Functionalized Disubstituted Polyacetylenes with High Light Refractivity: Synthesis through Polymer Reaction by Using Click Chemistry and Application as Precursors to Magnetic Nanoparticles (pages 2753–2761)

      Dr. Cathy K. W. Jim, Prof. Anjun Qin, Dr. Faisal Mahtab, Dr. Jacky W. Y. Lam and Prof. Ben Zhong Tang

      Version of Record online: 1 AUG 2011 | DOI: 10.1002/asia.201100286

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      Copper-catalyzed click! Ferrocene-functionalized disubstituted polyacetylenes are synthesized in high yields by Cu-catalyzed click reactions of azido-decorated poly(1-phenyl-1-hexyne) and poly(diphenylacetylene) with 1-ethynylferrocene.

    5. Chemical Probes

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      Chemical Modification and Organelle-Specific Localization of Orlistat-Like Natural-Product-Based Probes (pages 2762–2775)

      Peng-Yu Yang, Kai Liu, Chongjing Zhang, Grace Y. J. Chen, Yuan Shen, Mun Hong Ngai, Prof. Dr. Martin J. Lear and Prof. Dr. Shao Q. Yao

      Version of Record online: 8 JUL 2011 | DOI: 10.1002/asia.201100306

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      The chemical synthesis and biological evaluation of an expanded set of Orlistat-like compounds, and subsequent in situ proteome profiling and large-scale pull-down/LCMS analysis revealed many putative cellular targets (both common and unique) to these compounds in live HepG2 cells.

    6. Nanoparticles

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      Biofunctional Silicon Nanoparticles by Means of Thiol-Ene Click Chemistry (pages 2776–2786)

      Loes Ruizendaal, Sidharam P. Pujari, Veronique Gevaerts, Jos M. J. Paulusse and Han Zuilhof

      Version of Record online: 24 AUG 2011 | DOI: 10.1002/asia.201100375

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      Connecting the dots: Butylene-terminated fluorescent silicon nanoparticles (SiNPs) with an Si core size of 2.4 nm were synthesized (see graphic) and characterized in detail by NMR spectroscopy, IR, X-ray photoelectron, UV, and fluorescence analyses. Using thiol-ene chemistry, a broad range of functional molecules was covalently attached to the SiNPs.

    7. Click Chemistry

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      A Series of Hyperbranched Polytriazoles Containing Perfluoroaromatic Rings from AB2-Type Monomers: Convenient Syntheses by Click Chemistry under Copper(I) Catalysis and Enhanced Optical Nonlinearity (pages 2787–2795)

      Wenbo Wu, Yingjie Fu, Can Wang, Prof. Cheng Ye, Prof. Jingui Qin and Prof. Zhen Li

      Version of Record online: 22 AUG 2011 | DOI: 10.1002/asia.201100379

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      Self-assembly: Four new hyperbranched polytriazoles containing azo-chromophore moieties, derived from different AB2-type monomers, were successfully prepared through a click reaction under copper(I) catalysis by modifying the synthetic route.

    8. Ligand Effects

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      Sulfated Ligands for the Copper(I)-Catalyzed Azide–Alkyne Cycloaddition (pages 2796–2802)

      Dr. Wei Wang, Senglian Hong, Andrew Tran, Dr. Hao Jiang, Rebecca Triano, Dr. Yi Liu, Prof. Xing Chen and Prof. Peng Wu

      Version of Record online: 8 SEP 2011 | DOI: 10.1002/asia.201100385

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      Click into place: Two new tris(triazolylmethyl)amine-based ligands have been used for copper(I)-catalyzed azide–alkyne cycloaddition reactions in three bioconjugation applications: 1) labeling glycoproteins in crude cell lysates, 2) labeling glycoproteins on the surface of live mammalian cells, and 3) labeling surface proteins of live Escherichia coli (see scheme).

    9. Microarrays

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      Applying Small Molecule Microarrays and Resulting Affinity Probe Cocktails for Proteome Profiling of Mammalian Cell Lysates (pages 2803–2815)

      Haibin Shi, Mahesh Uttamchandani and Prof. Dr. Shao Q. Yao

      Version of Record online: 2 SEP 2011 | DOI: 10.1002/asia.201100523

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      Let's build a library! A small molecule microarray (SMM) constructed from a 284-member hydroxyethylamine-derived library is developed. By converting array-identified hits into affinity-based probes (AfBPs), subsequent large-scale proteome profiling experiments and pull-down/LC-MS analysis can be carried out. In addition to the expected cellular targets (e.g., cathepsin D), a number of putative off-targets are identified.

    10. Cycloadditions

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      Metal-Free 1,5-Regioselective Azide–Alkyne [3+2]-Cycloaddition (pages 2816–2824)

      Florian Kloss, Dr. Uwe Köhn, Dr. Burkhard O. Jahn, Dr. Martin D. Hager, Dr. Helmar Görls and Prof. Dr. Ulrich S. Schubert

      Version of Record online: 31 AUG 2011 | DOI: 10.1002/asia.201100404

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      Blatant favoritism! Substituted trimethylsilylalkynes enable high 1,5-regioselectivities in thermal metal-free azide–alkyne cycloadditions in aqueous media. The influence of azide and alkyne substituents on the regioisomeric ratios is low, but tuneable.

    11. Click Chemistry

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      Ligand-Assisted, Copper(II) Acetate-Accelerated Azide–Alkyne Cycloaddition (pages 2825–2834)

      Heather A. Michaels and Dr. Lei Zhu

      Version of Record online: 29 AUG 2011 | DOI: 10.1002/asia.201100426

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      A need for speed: Polytriazole ligands accelerate copper(II)-acetate-mediated azide–alkyne cycloaddition with unactivated, nonchelating azides (see scheme). Kinetic investigations reveal a mechanistic dependence on the relative affinity of azide and alkyne to copper(II). We also offer evidence for the mechanistic synergy between the title reaction and the alkyne oxidative homocoupling reaction.

    12. Bioconjugates

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      Construction of Polymer–Protein Bioconjugates with Varying Chain Topologies: Polymer Molecular Weight and Steric Hindrance Effects (pages 2835–2845)

      Dr. Xuejuan Wan, Prof. Guoying Zhang, Prof. Zhishen Ge, Prof. Ravin Narain and Prof. Shiyong Liu

      Version of Record online: 2 SEP 2011 | DOI: 10.1002/asia.201100489

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      Shooting stars: The steric hindrance effects were systematically explored for well-defined synthetic polymer–protein bioconjugates with varying chain architectures constructed from avidin and biotinylated precursors site-specifically labeled with a single biotin moiety at the chain terminal, chain middle, or diblock junction point (see picture).

  9. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Focus Reviews
    8. Communications
    9. Full Papers
    10. Preview
    1. You have free access to this content
      Preview: Chem. Asian J. 11/2011 (page 2847)

      Version of Record online: 28 SEP 2011 | DOI: 10.1002/asia.201190044

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