- Modified Nucleobases with Uniform H-Bonding Interactions, Homo- and Hetero-Basepair Bias, and Mismatch Discrimination
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Described herein are divalent nucleobases that each binds two nucleic acid strands, matched or mismatched when incorporated into a nucleic acid or nucleic acid analog backbone, such as in a γ-peptide nucleic acid (γPNA). Also provided are genetic recognition reagents comprising one or more of the divalent nucleobases and a nucleic acid or nucleic acid analog backbone, such as a γPNA backbone. Uses for the divalent nucleobases and monomers and genetic recognition reagents containing the divalent nucleobases also are provided.
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Paragraph 0014
(2021/07/30)
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- Triazolo-peptidomimetics: novel radiolabeled minigastrin analogs for improved tumor targeting
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MG11 is a truncated analog of minigastrin, a peptide with high affinity and specificity toward the cholecystokinin-2 receptor (CCK2R), which is overexpressed by different tumors. Thus, radiolabeled MG11 derivatives have great potential for use in cancer d
- Grob, Nathalie M.,H?ussinger, Daniel,Deupi, Xavier,Schibli, Roger,Behe, Martin,Mindt, Thomas L.
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supporting information
p. 4484 - 4495
(2020/06/08)
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- Straightforward Entry to S -Glycosylated Fmoc-Amino Acids and Their Application to Solid Phase Synthesis of Glycopeptides and Glycopeptidomimetics
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Streamlined access to S-glycosylated Fmoc-amino acids was developed. The process provides diverse glycosylated modified amino acids in high yield and stereoselectivity taking advantage of the in situ generation of a glycosylthiolate obtained from carbohyd
- Comegna, Daniela,De Paola, Ivan,Saviano, Michele,Del Gatto, Annarita,Zaccaro, Laura
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p. 640 - 643
(2015/03/05)
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- A peptide aldehyde microarray for high-throughput profiling of cellular events
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Microarrays provide exciting opportunities in the field of large-scale proteomics. With the aim to elucidate enzymatic activity and profiles within native biological samples, we developed a microarray comprising a focused positional-scanning library of enzyme inhibitors. The library was diversified across P1-P4 positions, creating 270 different inhibitor sublibraries which were immobilized onto avidin slides. The peptide aldehyde-based small-molecule microarray (SMM) specifically targeted cysteine proteases, thereby enabling large-scale functional assessment of this subgroup of proteases, within fluorescently labeled samples, including pure proteins, cellular lysates, and infected samples. The arrays were shown to elicit binding fingerprints consistent with those of model proteins, specifically caspases and purified cysteine proteases from parasites (rhodesein and cruzain). When tested against lysates from apoptotic Hela and red blood cells infected with Plasmodium falciparum, clear signatures were obtained that were readily attributable to the activity of constituent proteases within these samples. Characteristic binding profiles were further able to distinguish various stages of the parasite infection in erythrocyte lysates. By converting one of our brightest microarray hits into a probe, putative protein markers were identified and pulled down from within apoptotic Hela lysates, demonstrating the potential of target validation and discovery. Taken together, these results demonstrate the utility of targeted SMMs in dissecting cellular biology in complex proteomic samples.
- Wu, Hao,Ge, Jingyan,Yang, Peng-Yu,Wang, Jigang,Uttamchandani, Mahesh,Yao, Shao Q.
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supporting information; scheme or table
p. 1946 - 1954
(2011/04/16)
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- A facile synthesis and crystallographic analysis of N-protected β-amino alcohols and short peptaibols
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A facile, efficient and racemization-free method for the synthesis of N-protected β-amino alcohols and peptaibols using N-hydroxysuccinimide active esters is described. Using this method, dipeptide, tripeptide and pentapeptide alcohols were isolated in high yields. The conformations in crystals of β-amino alcohol, dipeptide and tripeptide alcohols were analysed, with a well-defined type III β-turn being observed in the tripeptide alcohol crystals. This method is found to be compatible with Fmoc-, Boc- and other side-chain protecting groups.
- Jadhav, Sandip V.,Bandyopadhyay, Anupam,Benke, Sushil N.,Mali, Sachitanand M.,Gopi, Hosahudya N.
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supporting information; experimental part
p. 4182 - 4187
(2011/06/28)
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- Simple and efficient synthesis of Fmoc/Boc/Cbz-protected-β-amino alcohols and peptidyl alcohols employing Boc2O
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An efficient method for the activation of Fmoc/Boc/Cbz-protected amino acids using Boc2O and the reduction of the in situ generated carbonic-carbonic anhydride to their corresponding 1β-amino alcohols using sodium borohydride has been described. The method is simple, rapid and free from racemization. Besides, the protocol is also extended for the conversion of N-urethane protected peptide acids to their corresponding alcohols. Copyright
- Lalithamba,Sureshbabu, Vommina V.
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experimental part
p. 1372 - 1378
(2011/01/13)
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- Tin(ii) chloride assisted synthesis of N-protected γ-amino β-keto esters through semipinacol rearrangement
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A facile synthetic route for the preparation of N-protected γ-amino β-keto esters from amino aldehydes and ethyl diazoacetate is described. The two component coupling is facilitated by tin(ii) chloride followed by semipinacol rearrangement leading to the product in quantitative yield. The reaction is mild, instantaneous and compatible with Boc-, Fmoc- and Cbz-amino protecting groups.
- Bandyopadhyay, Anupam,Agrawal, Neha,Mali, Sachitanand M.,Jadhav, Sandip V.,Gopi, Hosahudya N.
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supporting information; experimental part
p. 4855 - 4860
(2010/12/24)
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- Synthesis of thioureido-linked peptidomimetics, glycosylated amino acids, and neoglycoconjugates using bis(benzotriazolyl)methanethione as thioacylating agent
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A practical synthesis of thiourea-linked peptidomimetics, glycosylated amino acids, and neoglycoconjugates is described employing bis(benzotriazolyl) methanethione as thiocarbonylating reagent. The entire protocol is mild, efficient, high-yielding, and free from hazardous reagents. All the intermediates and products have been isolated and fully characterized by 1H NMR, 13C NMR, and mass spectrometry. Georg Thieme Verlag Stuttgart ? New York.
- Sureshbabu, Vommina V.,Chennakrishnareddy, Gundala,Hemantha, Hosahalli P.
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body text
p. 715 - 720
(2010/06/14)
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- click synthesis of small-molecule inhibitors targeting caspases
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A panel of 198 P4-diversified aldehyde (reversible) and vinyl sulfone (irreversible) inhibitors is successfully synthesized via an efficient click chemistry platform and directly screened against caspase-3 and -7 for inhibition. The Royal Society of Chemistry.
- Ng, Su Ling,Yang, Peng-Yu,Chen, Kitty Y.-T.,Srinivasan, Rajavel,Yao, Shao Q.
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supporting information; scheme or table
p. 844 - 847
(2008/10/09)
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- Solid-phase synthesis of azidomethylene inhibitors targeting cysteine proteases
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An efficient strategy for the solid-phase synthesis of azidomethylene inhibitors targeting cysteine proteases is described. The method is highlighted by its compatibility with readily available building blocks, as well as its ability to accommodate differ
- Yang, Peng-Yu,Wu, Hao,Lee, Mei Yin,Xu, Ashley,Srinivasan, Rajavel,Yao, Shao Q.
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supporting information; experimental part
p. 1881 - 1884
(2009/04/18)
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- Synthesis of N-urethane protected β-amino alcohols employing N-(protected-α-aminoacyl)benzotriazoles
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A simple and racemisation-free synthesis of N-urethane protected α-amino/peptidyl alcohols by the reduction of the corresponding easily accessible N-acylbenzotriazoles is described. The method is practical, straightforward, fast and efficient for the synt
- Sureshbabu, Vommina V.,Sudarshan,Muralidhar,Narendra
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p. 683 - 685
(2008/09/20)
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- Reduction of pentafluorophenyl esters to the corresponding primary alcohols using sodium borohydride
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Primary alcohols and chiral N-protected 2-amino alcohols can be obtained in high yields from the reaction of pentafluorophenyl esters of the corresponding carboxylic acids with sodium borohydride in THF under mild conditions. This reductive method is rapid and compatible with various functional groups as well as with the most common N-protective groups Z, Boc and Fmoc.
- Papavassilopoulou, Eleni,Christofis, Petros,Terzoglou, Despina,Moutevelis-Minakakis, Panagiota
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p. 8323 - 8325
(2008/04/13)
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- DMSO-aided o-iodoxybenzoic acid (IBX) oxidation of Fmoc-protected amino alcohols
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A fast and highly convenient procedure for the formation of Fmoc-protected amino aldehydes from the corresponding alcohols using 1.1 equiv. of IBX in the presence of dimethylsulfoxide (DMSO) is discussed. This procedure leads to the clean synthesis of Fmo
- Chen, Jack J.,Aduda, Vince
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p. 3493 - 3499
(2008/03/13)
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- Discovery and structure-activity relationship of antagonists of B-cell lymphoma 2 family proteins with chemopotentiation activity in vitro and in vivo
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Development of a rationally designed potentiator of cancer chemotherapy, via inhibition of Bcl-XL function, is described. Lead compounds generated by NMR screening and directed parallel synthesis displayed sub-μM binding but were strongly deactivated in the presence of serum. The dominant component of serum deactivation was identified as domain III of human serum albumin (HSA); NMR solution structures of inhibitors bound to both Bcl-X L and HSA domain III indicated two potential optimization sites for separation of affinities. Modifications at both sites resulted in compounds with improved Bcl-XL binding and greatly increased activity in the presence of human serum, culminating in 73R, which bound to Bcl-XL with a Ki of 0.8 μM. In a cellular assay 73R reversed the protection afforded by Bcl-XL overexpression against cytokine deprivation in FL5.12 cells with an EC50 of 0.47 μM. 73R showed little effect on the viability of the human non small cell lung cancer cell line A549. However, consistent with the proposed mechanism, 73R potentiated the activity of paclitaxel and UV irradiation in vitro and potentiated the antitumor efficacy of paclitaxel in a mouse xenograft model.
- Wendt, Michael D.,Shen, Wang,Kunzer, Aaron,McClellan, William J.,Bruncko, Milan,Oost, Thorsten K.,Ding, Hong,Joseph, Mary K.,Zhang, Haichao,Nimmer, Paul M.,Ng, Shi-Chung,Shoemaker, Alexander R.,Petros, Andrew M.,Oleksijew, Anatol,Marsh, Kennan,Bauch, Joy,Oltersdorf, Tilman,Belli, Barbara A.,Martineau, Darlene,Fesik, Stephen W.,Rosenberg, Saul H.,Elmore, Steven W.
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p. 1165 - 1181
(2007/10/03)
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- Solid phase synthesis of selective caspase-3 peptide inhibitors
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A robust method for the solid phase synthesis of a series of selective caspase-3 peptide inhibitors is described. The inhibitors can be obtained after cleavage from the solid support without further purification.
- Grimm, Erich L.,Roy, Bruno,Aspiotis, Renee,Bayly, Christopher I.,Nicholson, Donald W.,Rasper, Dita M.,Renaud, Johanne,Roy, Sophie,Tam, John,Tawa, Paul,Vaillancourt, John P.,Xanthoudakis, Steven,Zamboni, Robert J.
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p. 845 - 851
(2007/10/03)
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- Gamma-ketoacid tetrapeptides as inhibitors of caspase-3
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The invention encompasses the novel class of compounds represented by formula I, which are caspase-3 inhibitors. The invention also encompasses certain pharmaceutical compositions for treatment of caspase-3 mediated diseases comprising compounds of formula I.
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- Pyrazinones, compositions containing such compounds and methods of use
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Compounds represented by formula I: as well as pharmaceutically acceptable salts, esters, N-oxides and hydrates thereof are disclosed. Pharmaceutical compositions and methods of use are also included. The compounds are active against the caspase-3 enzyme, and thus are useful to treat fin caspase-3 mediated diseases and conditions.
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- Solid-phase synthesis of oligourea peptidomimetics employing the Fmoc protection strategy
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A solid-phase-Fmoc-based-synthesis strategy is described for oligourea peptidomimetics as well as a convenient general synthesis approach for the preparation of the required building blocks 5a-j and 5k. These are suitable for use in peptide or robot synthesizers, which is illustrated by the synthesis of oligourea peptidomimetics of part of Leu-enkephalin (10) and a neurotensin derivative (17).
- Boeijen,Van Ameijde,Liskamp
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p. 8454 - 8462
(2007/10/03)
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- Solid-phase synthesis of new S-glycoamino acid building blocks.
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Efficient synthesis of unprotected S-glycoamino acid building blocks in the solid phase by coupling a sugar 1-thiolate with iodine activated fluoren-9-ylmethoxycarbonyl (Fmoc) protected amino acids.
- Jobron,Hummel
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p. 2265 - 2267
(2007/10/03)
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- Solid phase syntheses of oligoureas
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Isocyanates 7 were formed from monoprotected diamines 3 or 6, which in turn can be easily prepared from commercially available N-BOC- or N-FMOC-protected amino acid derivatives. Isocyanates 7, formed in situ, could be coupled directly to a solid support f
- Burgess, Kevin,Ibarzo, Javier,Linthicum, D. Scott,Russell, David H.,Shin, Hunwoo,Shitangkoon, Aroonsiri,Totani, Reiko,Zhang, Alex J.
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p. 1556 - 1564
(2007/10/03)
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- A facile synthesis of chiral N-protected β-amino alcohols
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Chiral N-protected β-amino alcohols are easily obtained by NaBH4 reduction of mixed anhydrides of N-protected α-amino acids in an organic/aqueous medium. The alcohols obtained from side chain or main chain reduction of N-protected aspartic acid are converted in good yields into lactones.
- Rodriguez,Llinares,Doulut,Heitz,Martinez
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p. 923 - 926
(2007/10/02)
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