- Tandem deprotection/coupling for peptide synthesis in water at room temperature
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A tandem deprotection/coupling sequence is reported for solution-phase peptide synthesis in water under micellar catalysis conditions using the designer surfactant TPGS-750-M. Cbz deprotection followed by peptide coupling in the presence of COMU and 2,6-lutidine afforded polypeptides containing up to 10 amino acid residues. A broad scope characterizes this new technology. No epimerization has been detected. The associated E Factors, as a measure of "greenness" and known to be extremely high for peptide couplings, have been reduced to less than 10 due to the step-economy and minimal amounts of organic solvent needed for product extraction.
- Cortes-Clerget, Margery,Berthon, Jean-Yves,Krolikiewicz-Renimel, Isabelle,Chaisemartin, Laurent,Lipshutz, Bruce H.
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supporting information
p. 4263 - 4267
(2017/09/28)
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- Metalloporphyrin receptors for histidine-containing peptides
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Two new ditopic metalloporphyrin receptors constructed by combining metalloporphyrin with crown ethers have been prepared and characterized. 1H NMR and MS spectra confirmed the complexation of receptor with peptide driven by coordination interaction and hydrogen bonding. UV/vis experiments revealed that the receptors exhibited high binding affinity to histidine-containing peptides. These receptors could differentiate short peptides of C-terminal histidine and N-terminal histidine and formed the most stable complexes with tripeptide.
- Liu, Hui,Li, Zhan-Ting
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supporting information
p. 659 - 662
(2014/06/09)
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- Synthesis of dipeptides from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione activated α-amino acids
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A simple two step procedure for the synthesis of a dipeptide from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione (HO-ASUD) activated α-amino acids is described. In presence of DCC, N-hydroxy-3-azaspiro[5,5]undecane-2,4- dione readily esterifies the carboxylic acid group of all the N-protected amino acids to yield crystalline N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy ester. The N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy esters of N-protected amino acids readily condensed with other amino acids and gave a dipeptide. This new method is effective for the DCC coupling of a variety of chiral amino acids without loss of enantiomeric purity. Synthesis of fifteen dipeptides including the hitherto unreported Fmoc-l-Orn(Boc)-Val-OMe, Fmoc-l-Cys(trt)-Gly-OEt and Boc-l-Tyr-Gly-OEt is presented.
- Nowshuddin, Shaik,Ram Reddy
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scheme or table
p. 22 - 25
(2011/04/18)
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- Bromelain catalyzed synthesis of peptides in organic solvent
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For the first time, immobilized bromelain was shown to maintain high catalytic activity in organic solvent and to form peptide bonds. It requires only 7 hours to obtain Cbz-Gly-L-Leu-OMe in 85% yield. The precursor of aspartame (Cbz-L-Asp-L-Phe-OMe) and other dipeptides were also synthesized by this method.
- Tai, Dar-Fu,Fu, Shu-Lin
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p. 179 - 183
(2007/10/03)
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- New system for peptide synthesis using N-acylpyrazoles
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New system of peptide synthesis was described. The extension of one amino acid unit on the peptide chain was constituted from only 2 reaction steps, the conversion from esters to the corresponding N-acylpyrazoles and the subsequent aminolysis with amino esters. This new system was distinctive from the conventional peptide synthesis, which was consisted of 3 steps of the deprotection, the activation and the condensation. Moreover, the key intermediate N-acylpyrazoles exhibited the excellent properties of high sensitivity and separability for the chiral column on HPLC using the UV detector.
- Kashima, Choji,Tsuruoka, Shiro,Mizuhara, Saori
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p. 413 - 424
(2007/10/03)
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- Preparation of carboxamides via carboxylic-phosphoric anhydrides
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A number of reagents used to prepare carboxamides via a carboxylic-phosphoric anhydride intermediate have been reexamined. It was found that a simple carboxylic-phosphoric anhydride prepared from a carboxylic acid and commercially available diethyl chlorophosphate provided several significant advantages over more complex intermediates in many cases.
- Gaede, Bruce
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- Rapid, one-pot synthesis of urethane-protected tripeptides
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Urethane-protected tripeptides are synthesized in solution, without isolation of purification of intermediates, using urethane-protected N-carboxyanhydrides as coupling reagents and hydrogenation for removal of N-protection.
- Zhu, Yun-Fei,Fuller, William D.
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p. 807 - 810
(2007/10/02)
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- Enol esters as intermediates for the facile conversion of amino acids into amides and dipeptides
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N-Protected amino enol esters are easily transformed at room temperature into amino amides, and in the presence of potassium cyanide as catalyst, into tertiary amides and dipeptides.
- Kabouche,Bruneau,Dixneuf
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p. 5359 - 5362
(2007/10/02)
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- KINETICS OF THE ALKALINE HYDROLYSIS OF SEVERAL N-BENZYLOXYCARBONYLDIPEPTIDE METHYL AND ETHYL ESTERS
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The reaction rates of the alkaline hydrolysis of synthesized N-protected dipeptide methyl and ethyl esters were studied systematically.From the kinetic data the energies of activation, the pre-exponential factors and the reference values at 40 deg C were calculated.The rate of hydrolysis shows to be strongly dependent on the C-terminal amino acid in the sequence Gly >> Ala/Met/Phe > Leu >> Val/Pro.Surprisingly the N-terminal amino acid also exerts an effect, but in a different sequence.N-Terminal Phe in particular shows a relative accelerating effect.Remarkable is the significantly faster ester hydrolysis of glycine containing dipeptide ethyl esters in ethanol/water compared to the corresponding methyl esters in methanol/water.
- Hoogwater, D. A.,Peereboom, M.
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p. 5325 - 5332
(2007/10/02)
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- Activation of Dithiocarbamate by 2-Halothiazolium Salts
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Activation of dithiocarbamate salts with 2-halo-3-alkyl-4-phenylthiazolium salt and subsequent one-pot nucleophilic reaction with N, S, and O nucleophiles provided substituted thioureas, dithiocarbamates, and thiocarbamates or amides, respectively, under very mild conditions.A useful thiocarbonyl-transfer reaction is also described that consists of activation of imidazolodithiocarbamate and a subsequent one-pot nucleophilic reaction. (Thiocarbonyl)diimidazole is generated in situ.
- Sugimoto, Hirohiko,Makino, Itsuo,Hirai, Kentaro
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p. 2263 - 2267
(2007/10/02)
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- PREPARATION OF ESTERS OF AMINO ACIDS AND OF PEPTIDES UNDER MILD CONDITION
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A new method of obtaining esters of N-protected amino acids and peptides from complexes of their sodium salts with 15-crown-5 that are soluble in organic solvents is proposed.
- Mazurov, A. A.,Antonenko, S. V.,Andronati, S. A.
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p. 208 - 210
(2007/10/02)
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- A New Synthesis of Peptides from Azides and Unactivated Carboxylic Acids
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The title reaction, in which an azido compound is treated first with a tertiary phosphine, followed by warming in an inert solvent with a carboxylic acid, has been used to synthesize a number of small peptides and appears from mechanistic studies to proceed via a pentacoordinate phosphorus intermediate.
- Zaloom, Jeffrey,Calandra, Michael,Roberts, David C.
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p. 2601 - 2603
(2007/10/02)
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- THE CINNAMYLOXYCARBONYL GROUP AS A NEW AMINO-PROTECTING GROUP
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A new urethane-type protecting group for amines, cinnamyloxycarbonyl (Coc) group, is described.The cleavage of the Coc group is effectively catalyzed by 5 molpercent of in the presence of formic acid, pyridine, and N-hydroxysuccinimide in ref
- Kinoshita, Hideki,Inomata, Katsuhiko,Kameda, Takuo,Kotake, Hiroshi
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p. 515 - 518
(2007/10/02)
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- Process for acylation with novel acylating agent
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This invention relates to a novel acylation process which comprises using as the acylating agent an o-hydroxy-substituted aromatic oxime ester represented by the general formula (I) STR1 and mixing said acylating agent with an amine substance represented
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- THE SYNTHESIS OF AMIDES, ESTERS, AND THIOESTERS
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Diethyl 2-(3-oxo-2,3-dihydro-1,2-benzisosulfonazolyl)phosphonate is a highly reactive condensing agent, which provides good yield route to amides, esters, and thioesters from a variety of amines, active hydroxylamines, and thiols and acids.
- Miyake, Muneharu,Kirisawa, Makoto,Tokutake, Norio
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p. 123 - 126
(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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- Reactivity of Aromatic o-Hydroxy Oximes. II. The Use of Esters of Aromatic o-Hydroxy Oximes in Peptide Synthesis
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Esters of N-protected amino acids with o-hydroxybenzaldehyde oxime, o-hydroxyacetophenone oxime, o-hydroxybenzophenone oxime, and their 5-Cl and 5-NO2 derivatives were prepared by several methods.Various dipeptide derivatives with high purity were obtaine
- Hayashi, Ikuo,Shimizu, Kiyoshi
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p. 3197 - 3198
(2007/10/02)
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- Process for the preparation of carboxylic acid amides and peptides
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What is disclosed is a method of making a carboxylic acid amide, including a peptide, by reacting a compound having a free amino group with a compound having a free carboxy group in the presence of an anhydride of an alkane-phosphonic acid.
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- STUDIES ON AMINO ACIDS AND PEPTIDES-III. 2,4-BIS(4-METHOXYPHENYL)-1,3,2,4-DITHIADIPHOSPHETANE 2,4-DISULFIDE, LR, AS A NEW RACEMIZATION FREE COUPLING REAGENT IN PEPTIDE SYNTHESIS
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The easily accesable 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, LR, has been reacted with salts of N-protected amino acids 1 (Z-Gly-OH, Boc-Gly-OH, Boc-S-Ser(Bzl)-OH, Bos-S-Tyr(Bzl)-OH, Z-S-Arg(Z2)-OH, and Z-S-Pro-OH), at room tem
- Pedersen, U.,Thorsen, M.,El-Khrisy, E. -E. A. M.,Clausen, K.,Lawesson, S. -O.
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p. 3267 - 3269
(2007/10/02)
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- Derivatives of 1,3,5-Triazine: Part III - Cyanuric Chloride-Dimethylformamide as a New Reagent for Synthesis of Amides, Esters, Aldehydes and for Dehydration Reactions
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Cyanuric chloride reacts with dimethylformamide to form a complex (I), which can be used directly for the synthesis of amides, esters, relatively simple peptides, aldehydes and for dehydration reactions.
- Lahoti, R. J.,Wagle, D. R.
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p. 1007 - 1008
(2007/10/02)
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- 5-Nitro-3H-1,2-benzoxathiole SS-Dioxide, a New Reagent for Coupling in Peptide Synthesis
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Peptides are rapidly prepared and isolated by a two-step, one-pot reaction using 5-nitro-3H-1,2-benzoxathiole SS-dioxide (1), a strained sultone, as a condensation agent.
- Wakselman, Michel,Acher, Francine
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p. 632 - 634
(2007/10/02)
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- REACTION OF CARBOXYLATE SALTS WITH CYCLIC PHOSPHORAMIDATES : AMIDE BOND FORMATION BY PRIOR AMINE CAPTURE
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Tri- or tetraalkyl-ammonium carboxylates react with 2-alkylamino-2-oxo-1,3,2-benzodioxaphospholes at 25 deg C to give amides or peptides, probably by a nucleophilic attack on phosphorous followed by a cascade of intramolecular acyl transfer reaction.
- Wakselman, M.,Acher, F.
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p. 2705 - 2708
(2007/10/02)
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- Process for acylation of amino, imino and hydroxyl groups using pyrimidine derivatives
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Pyrimidine derivatives represented by the formula, SPC1 Wherein R1 and R2 are individually a hydrogen atom or a methyl group, and R3 is a group formed by removing the carboxyl group from a carboxylic acid, are quite useful in acylating compounds having amino and/or imino and/or hydroxyl groups. The pyrimidine derivatives can easily be prepared by reacting a 2-mercapto-4- and/or 6-methyl-substituted or unsubstituted pyrimidine with a carboxylic acid or a reactive derivative thereof in an inert solvent.
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