- Spontaneous and promoted association of linear oligoglycines
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Linear oligoglycines of various lengths bearing a carboxyl or an amide group at their C-termini and also their poly(acrylamide) conjugates were synthesized. No self-assembly into supramolecular structures was observed for free oligoglycines H-(Gly)m-OH (m = 3-5). At the same time, oligoglycylamides H-(Gly)m-NH2 (m = 3-5) demonstrated ability for both self-assembly in aqueous solution and assembly promoted by an additional interaction with surface. In the case of polymer-bound oligoglycines (and their amides), no intramolecular clustering of peptide chains, as expected, was observed. This means that the presence of several oligoglycine chains bound to each other in one center is not a necessary prerequisite for polyglycine II-type association. Pleiades Publishing, Inc., 2006.
- Gorokhova,Chinarev,Tuzikov,Tsygankova,Bovin
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- Multivalent glycomimetics: synthesis of nonavalent mannoside clusters with variation of spacer properties
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Oligosaccharide mimetics are important tools in the glycosciences. In this work, we have employed spaced glycodendrons for the synthesis of oligomannoside mimetics. Starting from a number of trivalent, branched molecular wedges, the preparation of nonavalent cluster mannosides was accomplished, which were varied with regard to the chemical characteristics of their spacer moieties and spacer lengths. For ligation of the various trivalent dendrons to the nonavalent target molecules peptide coupling was employed.
- Patel, Anupama,Lindhorst, Thisbe K.
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- Supra-blot: An accurate and reliable assay for detecting target proteins with a synthetic host molecule-enzyme hybrid
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In accordance with the rapid increase in demand for selective and spatial chemical tagging, and accurate detection of proteins of interest, we develop a sensitive protein detection method, termed "Supra-blot" capitalizing on high-affinity host-guest interaction between cucurbit[7]uril (CB[7]) and adamantylammonium (AdA). The method can directly detect chemically tagged proteins without false-positive signals caused by endogenous biomolecules. Not only a single specific protein, but also spatially localized proteins in cells were labeled with AdA, and selectively detected by a host molecule-enzyme hybrid, CB[7]-conjugated horseradish peroxidase (CB[7]-HRP) generating amplified chemiluminescence signals. This study shows the great potential of Supra-blot for accurate and reliable detection of proteins of interest in cells.
- Sung, Gihyun,Lee, Song-Yi,Kang, Myeong-Gyun,Kim, Kyung Lock,An, Jaeyeon,Sim, Jaehwan,Kim, Sungwan,Kim, Seungjoon,Ko, Jaewon,Rhee, Hyun-Woo,Park, Kyeng Min,Kim, Kimoon
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- DEGRADABLE POLYETHYLENE GLYCOL DERIVATIVE
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The invention provides a high-molecular-weight polyethylene glycol derivative that does not cause vacuolation of cells. The degradable polyethylene glycol derivative is represented by the following formula (1): wherein m is 1-7, n1 and n2 are each independently 45-682, p is 1-4, R is an alkyl group having 1-4 carbon atoms, Z is an oligopeptide with 2-8 residues composed of neutral amino acids excluding cysteine, Q is a residue of a compound having 2-5 active hydrogens, X is a functional group capable of reacting with a bio-related substance, and L1, L2, L3, L4 and L5 are each independently a single bond or a divalent spacer.
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Paragraph 0428; 0429; 0430
(2021/05/21)
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- Addition of HO-Acids to N,N-Bis(oxy)enamines: Mechanism, Scope and Application to the Synthesis of Pharmaceuticals
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The regioselectivity of the addition of HO-acids to the activated π bond in N,N-bis(oxy)enamines has been found to be dramatically dependent upon the solvent. Mechanistic investigations and quantum-chemical calculations revealed that solvent affects the reaction pathway. In basic solvents (DMF, NMP, DMSO), N,N-bis(oxy)enamines were converted into nitrosoalkenes by a Lewis base promoted process followed by oxy-Michael addition of the HO-acid. In non-polar solvents (toluene, CH2Cl2), the reaction occurs by an acid-promoted SN′ substitution of the N-oxy-group via a highly reactive N-vinyl-N-alkoxynitrenium species. Based on these studies, general and efficient protocols for the oximinoalkylation of various HO-acids (carboxylic acids, phenols, hydroxamic, phosphoric and sulfonic acids) employing readily available N,N-bis(oxy)enamines were developed. These methods proved to be applicable to the post-modification of natural molecules bearing acidic OH groups (such as steroidal hormones, bile acids, protected amino acids and peptides) and ligands (BINOL). The resulting α-oxyoximes were demonstrated to be useful precursors of valuable 1,2-amino alcohol or 1,2-hydroxylamino alcohol derivatives, including the antiarrhythmic drug Mexiletine and a potent matrix metalloproteinase inhibitor.
- Naumovich, Yana A.,Golovanov, Ivan S.,Sukhorukov, Alexey Yu.,Ioffe, Sema L.
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p. 6209 - 6227
(2017/11/15)
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- Guanidine hydrochloride as an organocatalyst for N-Boc protection of amino groups
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A simple and efficient method for the chemoselective N-Boc protection of the amine moiety in a variety of compounds is described using di-tert-butyl dicarbonate and guanidine hydrochloride as an organocatalyst in ethanol at 35-40°C. Selective mono-N-Boc protection of diamines and chemoselective protection of hydroxylamines without formation of any side products is achieved. Amino acids and peptides are N-Boc protected efficiently in excellent yields under convenient reaction conditions.
- Jahani, Fatemeh,Tajbakhsh, Mahmood,Golchoubian, Hamid,Khaksar, Samad
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supporting information; experimental part
p. 1260 - 1264
(2011/04/15)
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- Internally quenched peptides for the study of lysostaphin: An antimicrobial protease that kills Staphylococcus aureus
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Lysostaphin (EC. 3.4.24.75) is a protein secreted by Staphylococcus simulans biovar staphylolyticus and has been shown to be active against methicillin resistant S. aureus (MRSA). The design and synthesis of three internally quenched substrates for lysost
- Warfield, Rachel,Bardelang, Philip,Saunders, Helen,Chan, Weng C.,Penfold, Christopher,James, Richard,Thomas, Neil R.
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p. 3626 - 3638
(2008/10/09)
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- Syntheses of fluorescence-labeled artificial leaf-opening substances, fluorescent probe compounds useful for bioorganic studies of nyctinasty
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In a previous paper, the syntheses of potassium galactolespedezate (1) and potassium galactoisolespedezate (2), artificial leaf-opening substances useful for bioorganic studies of nyctinasty were reported. The fluorescent probe compounds, fluorescence-labeled galactoisolespedezates (3, 10, 13), designed on the basis of 1 and 2, were prepared. In particular, compound 3 was bioactive at 5 x 10-5 M, one-fiftieth as strong as the natural leaf- opening substance. This fluorescent probe would be useful for bioorganic studies of nyctinasty. (C) 2000 Elsevier Science Ltd.
- Ueda, Minoru,Sawai, Yoshiyuki,Yamamura, Shosuke
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p. 3433 - 3436
(2007/10/03)
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- Pretargeting methods and compounds
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Methods, compounds, compositions and kits that relate to pretargeted delivery of diagnostic and therapeutic agents are disclosed. In particular, methods for radiometal labeling of biotin, as well as related compounds, are described. Articles of manufactur
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- Pretargeting methods and compounds
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Methods, compounds, compositions and kits that relate to pretargeted delivery of diagnostic and therapeutic agents are disclosed. In particular, methods for radiometal labeling of biotin, as well as related compounds, are described. Articles of manufacture useful in pretargeting methods are also discussed.
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- Synthesis and properties of N(α)-(tert-butyloxycarbonyl)peptide p- guanidinophenyl esters as trypsin substrates
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N(α)-(tert-Butyloxycarbonyl)peptide p-guanidinophenyl esters were synthesized by amidination of N(α)-(tert-butyloxycarbonyl)peptide p- aminophenyl esters with 1-[N,N'-bis(benzyloxycarbonyl)amidino]pyrazole, followed by deprotection by catalytic hydrogenation, in good total yields. These synthetic esters were characterized as specific substrates for trypsin, and kinetic parameters for the trypsin-catalyzed hydrolysis are presented.
- Itoh,Sekizaki,Toyota,Tanizawa
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p. 2082 - 2087
(2007/10/03)
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- DNA-Binding Compounds. II. Synthesis of a Peptide-Linked Triacridine
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A novel peptide-linked triacridine (2) of the type (Acr)-A-C(Acr)-B-(Acr) has been synthesized in which the central trifunctional group () is 2,4-diaminobutyric acid (A2bu), spacer A is -γAbu-Tyr-Lys-Lys-Gly- and spacer B is -Gly-Gly-Gly-
- Mack, Philip O. L.,Kelly, David P.,Martin, Roger F.,Wakelin, Laurence P. G.
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- Conformations in the Solid State and Solubility Properties of Protected Homooligopeptides of Glycine and β-Alanine
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IR spectroscopic conformational analyses of Boc-Glyn-OBzl (n=3-7) and Boc-(β-Ala)n-OBzl (n=3-8) were performed in the solid state, suggesting the occurrence of the β-sheet structure in the higher oligomers (n=5-8).Solubility data ind
- Narita, Mitsuaki,Doi, Masamitsu,Kudo, Koji,Terauchi, Yusuke
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p. 3553 - 3558
(2007/10/02)
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- 1-Peptidyl derivatives of di-O-aminoglycosyl-1,3-diaminocyclitol antibacterial agents
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Disclosed herein are di-O-(aminoglycosyl)-1,3-diaminocyclitol antibacterial agents having on the 1-N-position of the 1,3-diaminocyclitol moiety a dipeptidyl or a tripeptidyl substituent. The compounds are useful antibacterial agents, as are their non-toxic pharmaceutically acceptable acid addition salts. Also disclosed are methods for preparing such agents from di-O-(aminoglycosyl)-1,3-diaminocyclitol antibacterial agents which are unsubstituted at the 1-N-position.
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- Fibrinopeptides. IV. Synthesis of human fibrinopeptide A
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Human fibrinopeptide A, a hexadecapeptide, released by the action of thrombin on fibrinogen during clotting of blood, has been synthesized by conventional methods. The synthetic peptide as well as some of the intermediates in the synthesis have been examined for anticoagulant activity. Though all of them were found to be active, the terminal carboxyl protected peptides are more potent inhibitors of clotting than the carboxyl free peptides.
- Channabasavaiah,Sivanandaiah
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p. 323 - 329
(2007/10/13)
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