- Measuring cell holding mechanism, and, a biosensor
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A measuring cell holding mechanism, comprising a measuring cell which is configured to include a dielectric block in which a flat face on which a ligand to be attached is formed, and a flow path member which constitutes a flow path between it and this flat face; a dielectric block pressing member which presses the dielectric block from the flow path member side; and a flow path member pressing member which presses the flow path member from the side opposite from the side on which the dielectric block is disposed, with a pressing force smaller than that by the dielectric block pressing member.
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- Organophosphorus esters of 1-hydroxy-2-phenylbenzimidazole: Synthesis and utilization as novel peptide coupling reagents
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Highly efficient coupling reagents - phosphoric acid diethyl ester 2-phenylbenzimidazol-1-yl ester, diphenylphosphinic acid 2-phenylbenzimidazol-1- yl ester and phosphoric acid diphenyl ester 2-phenylbenzimidazol-1-yl ester - were designed, synthesized and successfully applied in peptide coupling reactions. Their efficiency was evaluated through the synthesis of a range of amides and peptides, and the extent of racemization was studied by HPLC and found to be negligible. The mechanism of action is probably similar to those found for organophoshorus esters of hydroxybenzotriazole: a presumption supported by the isolation and characterization by mass spectrometry and 1H NMR of some of the proposed intermediates. Georg Thieme Verlag Stuttgart.
- Kokare, Nagnnath D.,Nagawade, Rahul R.,Rane, Vipul P.,Shinde, Devanand B.
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p. 766 - 772
(2008/01/04)
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- Peptide bond formation using polymer-bound BOP
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A new polymer-supported BOP (P-BOP) has been prepared starting from the commercially available polystyrene-bound 1-hydroxybenzotriazole (P-HOBt) and successfully used as a solid-supported reagent for peptide-coupling reactions. Compared to BOP, less epime
- Filip, Sorin V.,Lejeune, Valerie,Vors, Jean-Pierre,Martinez, Jean,Cavelier, Florine
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p. 1936 - 1939
(2007/10/03)
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- 2-Mercaptopyridine-1-oxide-based peptide coupling reagents
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The thiouronium salts S-(1-oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium hexafluorophosphate (HOTT) and tetrafluoroborate (TOTT), and S-(1-oxido-2-pyridinyl)-1,3-dimethyl-1,3-trimethylenethiouronium hexafluorophosphate (HODT) and tetrafluoroborate (TODT), prepared from 2-mercaptopyridine-1-oxide and 1,1,3,3-tetramethylurea (TMU) or 1,3-dimethylpropyleneurea (DMPU), have been employed as reagents in solution and solid-phase peptide coupling chemistry. Furthermore, 2-mercaptopyridine-1-oxide has been employed as racemization-reducing additive combined with the new thiouronium salts and other frequently used peptide coupling reagents such as DCC or TBTU.
- Albericio, Fernando,Bailén, Miguel A,Chinchilla, Rafael,Dodsworth, David J,Nájera, Carmen
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p. 9607 - 9613
(2007/10/03)
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- Polymer-bound TBTU as a new solid-supported reagent for peptide synthesis
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A new polymer-supported TBTU (P-TBTU) has been prepared from polystyrene-bound 1-hydroxybenzotriazole (P-HOBT) and used efficiently as a solid-supported reagent for peptide-coupling reactions, and is even effective with wet solvents. The P-HOBT can be rec
- Chinchilla, Rafael,Dodsworth, David J.,Nájera, Carmen,Soriano, José M.
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p. 2463 - 2466
(2007/10/03)
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- An activated phosphate for an efficient amide and peptide coupling reagent
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An activated phosphate for an efficient amide and peptide coupling reagent was discussed. Activation of diethyl phosphates was realized by attaching trifluoromethanesulfonanilide as an efficient leaving group and the phosphate proved to be a promising amide and peptide coupling reagent. Results showed that reactions of a primary amine with α-branched carboxylic acids and benzoic acid gave within 1 h the amides in quite high yield.
- Yasuhara, Tomohisa,Nagaoka, Yasuo,Tomioka, Kiyoshi
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p. 2901 - 2902
(2007/10/03)
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- 5-(1H-benzotriazol-1-yloxy)-3,4-dihydro-1-methyl 2H-pyrrolium hexachloroantimonate (BDMP): A highly efficient immonium type peptide coupling reagent
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HOBt-based immonium type coupling reagent, 5-(1H-benzotriazol-1-yloxy)-3,4-dihydro-1-methyl 2H-pyrrolium hexachloroantimonate (BDMP) has been designed, synthesized and utilized to synthesize oligopeptides and biologically active peptides both in solution
- Li, Peng,Xu, Jie Cheng
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p. 1163 - 1164
(2007/10/03)
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- BOMI - A novel peptide coupling reagent
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A novel coupling reagent, benzotriazol-1-yloxy-N,N- dimethylmethaniminium hexachloroantimonate (BOMI), was synthesized and successfully applied to the synthesis of oligopeptides, the racemization and the influence of several reaction parameters such as so
- Li, Peng,Xu, Jie Cheng
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p. 3605 - 3608
(2007/10/03)
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- New reactions of the thiocarbonyl function. The synthesis of hindered peptides
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The well-known radical chemistry of the thiocarbonyl function has been expanded to include the concerted reaction between an O-acyl derivative of N-hydroxypyridine-2(1H)-thione (a Barton PTOC ester) and a sulfenamide. The atom-economical process spawned a carboxamide and an unsymmetrical disulfide of synthetic and biological value. The reaction was successfully applied to the synthesis of sterically encumbered, urethane-protected dipeptides. The oxidation-reduction technology pertaining to the disulfide-phosphine combination facilitated the generation of transient Barton PTOC esters. In conjunction with the appropriate benzenesulfenamide, the Barton PTOC ester of benzoyl-L-leucine was shown to preserve optical integrity according to the sensitive Young test, albeit at low temperature. However, the thermodynamic forces at play are powerful and, as a result, the yields were not compromised. In all but the sterically demanding instances, the parent free amine almost matched the reaction time, yield, and enantiomeric excess of the corresponding benzenesulfenamide in its reaction with a Barton PTOC ester.
- Barton, Derek H. R.,Ferreira, J. Albert
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- N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters. Part II. Applications in peptide synthesis
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The N-hydroxypyridine-2(1H)-thione derivatives of two urethane-protected α-amino acids readily reacted with the α-amino acid esters or the corresponding benzenesulfenamides to give simple dipeptides in reasonable yields. The benzenesulfenamides are the re
- Barton, Derek H. R.,Ferreira, J. Albert
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p. 9367 - 9386
(2007/10/03)
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- A novel organophosphorus compound as a coupling reagent for peptide synthesis
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3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4 (3H)-one 1 is a new organophosphorus compound which can be used as an efficient coupling reagent for peptide synthesis by either solution or solid phase coupling.
- Fan, Chong-Xu,Hao, Xiao-Lin,Ye, Yun-Hua
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p. 1455 - 1460
(2007/10/03)
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- A fast procedure for the preparation of amides/peptides from carboxylic acids and azides via two redox reactions: Application to the synthesis of methionine enkephalin
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A one-pot self regulated approach for the synthesis of amides/peptides based on two reduction-oxidation (redox) reactions has been described. The primary and secondary amides/peptides are made by using azidotrimethylsilane and alkyl azides/α-azido acid de
- Ghosh, Sunil K.,Verma, Rekha,Ghosh, Usha,Mamdapur, Vasant R.
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p. 1705 - 1711
(2007/10/03)
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- Activation of N,N-bis(alkoxycarbonyl) amino acids. Synthesis of N-alkoxycarbonyl amino acid N-carboxyanhydrides and N,N-dialkoxycarbonyl amino acid fluorides, and the behavior of these amino acid derivatives
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Series of Boc- and Cbz-NCAs (2), and of N,N-bis(alkoxycarbonyl) amino acid fluorides U2AAFs (3) have been prepared by activation of N,N-bis-Boc- and N-Cbz,N-Boc-α-amino acids (1) with the Vilsmeier reagent or cyanuric fluoride. The absence of epimerization of 2 and 3 during both their formation and their coupling under standard conditions of peptide synthesis had been demonstrated by optical purity Young's tests. In other activated derivatives of bis-urethane protected activated amino acids, the exchangeability of the α-H is shown by the considerable racemization of Boc2Phe-OSu (8) in the presence of base, and by the formation of a Dakin-West type product 11 from the dipeptide Boc2Phe-Leu-OBn.
- Savrda, Jaroslav,Chertanova, Lyubov,Wakselman, Michel
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p. 5309 - 5322
(2007/10/02)
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- A low-epimerizing peptide coupling reagent based on the rearrangement of a carboxylic-sulfonic mixed anhydride
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A series of peptides has been prepared using an o-hydroxybenzenesulfonyl chloride as the condensation reagent. Experimentally, the coupling is a one pot two-steps reaction: formation and aminolysis of a substituted aryl ester. The first step occurs by an
- Cabaret, Daniel,Wakselman, Michel
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p. 9561 - 9564
(2007/10/02)
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- 2-Trifluoroacetylthiopyridine-1-Hydroxybenzotriazole: A Powerful Reagent for Peptide Synthesis
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A mixture of trifluoroacetylthiopyridine, the sodium salt of 1-hydroxybenzotriazole, and an acylamino acid is able to acylate amino acid esters in high yields with minimal racemization and should, therefore, be useful for fragment condensation reactions i
- Schmidt, Ulrich,Griesser, Helmut
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p. 1461 - 1462
(2007/10/02)
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- A new route to sequential polypeptides combining solid phase synthesis and solution peptide synthesis
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The cleavage of a resin-bound peptide from an oxime resin using the 2-phenacyloxyphenyl ester of an aminoacid provides a peptide with this aminoacid in C-terminal position. The inactive 2-phenacyloxyphenyl peptide ester thus obtained can then be converted into 2-hydroxyphenyl acts active ester. The polymerization of the repeat unit using this mode of activation gives sequential polypeptides of reasonable molecular weight and of high optical purity.
- Verhaeghe, Josette,Lacassie, Eric,Bertrand, Marylene,Trudelle, Yves
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p. 461 - 464
(2007/10/02)
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- A NEW CONVENIENT APPROACH TO PEPTIDE SYNTHESIS
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A new and highly efficient method based on a redox reaction using diphenyl diselenide and tributylphosphine for the general synthesis of peptides is described.The side reaction due to selenophenol formation is overcome by using chalcone as a scavenger or
- Singh, Usha,Ghosh, Sunil K.,Chadha, Mohindra S.,Mamdapur, Vasant R.
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p. 255 - 258
(2007/10/02)
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- SYNTHESIS OF N-PHOSPHORYL DI(OR TRI)-PEPTIDES THROUGH THE ACTIVE ESTER METHOD
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N-Phosphoryl di(or tri)-peptides were synthesized through the coupling of N-hydroxysuccinimide esters of N-phosphoryl amino acids with amino components.The active esters were prepared using ethyl dichlorophosphate (EDCP), diethyl phosphite (DEPH) or dicyc
- Ma, Xiao-Bo,Zhao, Yu-Fen
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- 2,2'-CARBONYL-BIS(3,5-DIOXO-4-METHYL-1,2,4-OXADIAZOLIDINE) : I- A NEW REAGENT FOR THE PREPARATION OF CARBAMATES AND AMIDES, APPLICATION TO THE SYNTHESIS OF DIPEPTIDES.
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2,2'-Carbonyl bis (3,5-dioxo-4-methyl-1,2,4-oxadiazolidine) was prepared and used for the synthesis of various carbamates and dipeptides.
- Denarie, Michel,Grenouillat, Denis,Malfroot, Thierry,Senet, Jean-Pierre,Sennyey, Gerard,Wolf, Patrick
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p. 5823 - 5826
(2007/10/02)
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- A SIMPLE METHOD FOR SYNTHESIS OF AMIDES AND PEPTIDES THROUGH ACYL CHLORIDES. A RAPID SYNTHESIS OF THYROTROPIN RELEASING HORMONE
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By improvement of the classical SOCl2-pyridine method for the preparation of acid chlorides, amides and optically pure peptides were synthesized rapidly in a simple manner from DCHA (dicyclohexylammonium) salts of carboxylic acids.This modified SOCl2-pyridine method was applied to a rapid synthesis of TRH.
- Matsuda, Fuyuhiko,Itoh, Shin,Hattori, Noritaka,Yanagiya, Mitsutoshi,Matsumoto, Takeshi
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p. 3625 - 3631
(2007/10/02)
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- BENZOTRIAZOL-1-YL DIETHYL PHOSPHATE. A NEW CONVENIENT COUPLING REAGENT FOR THE SYNTHESIS OF AMIDES AND PEPTIDES.
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Benzotriazol-1-yl diethyl phosphate is found to be a new convenient coupling reagent for the synthesis of amides and practically racemization-free peptides.
- Kim, Sunggak,Chang, Heung,Ko, Young Kwan
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p. 1341 - 1342
(2007/10/02)
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- Peptide-bond Formation, Chemoselective Acylation of Amino Acids, and Crosslinking Reaction between Amino Acids Utilizing a Functional Five-membered Heterocycle, 1,3-Thiazolidine-2-thione
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The monitored aminolysis of 3-acyl-1,3-thiazolidine-2-thiones has been extended to the peptide-bond formation, the chemoselective acylation of amino acids having multifunctional groups, and the crosslinking reaction between amino acids.
- Nagao, Yoshimitsu,Miyasaka, Tadayo,Seno, Kaoru,Fujita, Eiichi,Shibata, Daisuke,Doi, Etsushiro
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p. 2439 - 2446
(2007/10/02)
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- Additives Based on Liquid Crystal Forming Structure Elements for Suppressing Racemization in Peptide Synthesis by the DCC- and Mixed Anhydrides Methods
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A new type of additives suppressing racemization during peptide synthesis by the DCC- and mixed anhydrides methods are liquid crystal forming organic molecules or similar compounds with a specific long chain structure.The suppressing effect of the new additives was followed by the Anderson test, the modifid Young and n.m.r. tests.There was no racemization in a new Leu-enkephalin synthesis by the mixed anhydrides method with azoxybenzene as additive.
- Jeschkeit, H.,Strube, M.,Przybylski, J.,Miecznikowska, H.,Kupryszewski, G.
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p. 638 - 646
(2007/10/02)
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- Peptide Synthesis with Benzo- and Naphthosultones
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6-Nitro- and 6,8-dinitronaphth-1,2-oxathiole S,S-dioxides (7b and 7c) have been prepared from the parent naphthosultone 7a and compared with 5-nitrobenz-3H-1,2-oxathiole S,S-dioxide (1b) as coupling reagents for peptide synthesis.Nucleophilic attack of a carboxylate salt on these strained five-membered sultones leads to activated esters 3 and 9 which rapidly react with amines (except in the case of 9c).The rate constant for the formation of ester 9b is higher than that of 3b.Amides or peptides are formed in slightly better yields with the naphthosultone 7b than with the benzosultone 1b.The naphthosultones are also preferred over the benzosultones from the point of view of amount of 5(4H)-oxazolone formation from N-benzoyl amino acids and the degree of racemization.However the rate of alkaline hydrolysis of 7b is slower than that of 1b.All these results may be rationalized by a better intramolecular acyl transfer reaction in the more rigid mixed anhydride intermediate 8b.There is no dependence on in the rate equation for aminolysis of esters 3b and 9b by benzylamine in THF, acetonitrile, or DMF and the aminolysis is probably anchimerically assisted by a neighbouring S=O group.Esters 3b are more selective acylating agents for primary amino groups in the presence of secondary ones than esters 9b and this observation is exploited in a synthesis of maytenine by selective acylation of spermidine.
- Acher, Francine,Wakselman, Michel
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p. 4133 - 4138
(2007/10/02)
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- A CONVENIENT METHOD FOR THE SYNTHESIS OF CARBOXAMIDES AND PEPTIDES BY THE USE OF TETRABUTYLAMMONIUM SALTS
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Various carboxamides and peptides are prepared in good yields by treatment of free acids and amines in H2O-dichloromethane or aqueous THF with bis(o-nitrophenyl) phenylphosphonate in the presence of tetrabutylammonium hydrogen sulfate or bromide.Carboxylic esters are also successfully converted to amides via carboxylate salts in one-pot.
- Watanabe, Yutaka,Mukaiyama, Teruaki
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p. 285 - 288
(2007/10/02)
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- MONITORED AMINOLYSIS OF 3-ACYL-1,3-THIAZOLIDINE-2-THIONE WITH AMINO ACID AND ITS DERIVATIVE: PEPTIDE BOND FORMATION, CHEMOSELECTIVE ACYLATION, AND BRIDGING REACTION
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As a new extention of the monitored aminolysis of 3-acyl-1,3-thiazolidine-2-thione, its applications to peptide bond formation, chemoselective acylation of amino acid, and bridging reaction on the enzyme model are reported.
- Nagao, Yoshimitsu,Miyasaka, Tadayo,Seno, Kaoru,Yagi, Masahiro,Fujita, Eiichi
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p. 463 - 466
(2007/10/02)
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- Polymer-Bound Oxime Esters as Supports for Solid-Phase Peptide Synthesis. Preparation of Protected Peptide Fragments.
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A series of polystyrene-bound substituted benzophenone oximes (II) have been synthesized and tested as potential supports for the solid-phase preparation of protected peptide fragments.The polymer-bound p-nitrobenzophenone oxime (IID) has been found to be a suitable support for stepwise peptide synthesis.Protected peptides can be assembled on IID by coupling and deprotection steps similar to those employed in the usual Merrifield solid-phase procedures.Cleavage of peptides from IID can be accomplished with hydrazine and amino acid esters under mild conditionswhich do not affect benzyl ester side-chain protecting groups.The utility of IID has been illustrated in the synthesis of protected peptide hydrazides and esters, several of which have aspartic and glutamic acid side chains protected by benzyl groups.
- DeGrado, William F.,Kaiser, Emil Thomas
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p. 1295 - 1300
(2007/10/02)
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