- Enhancement of the small intestinal uptake of phenylalanylglycine via a H+/oligopeptide transport system by chemical modification with fatty acids
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The transport characteristics of chemically modified phenylalanylglycine (PheGly) with butyric acid (C4-Phe-Gly) and caproic acid (C6-Phe-Gly) were examined using rabbit intestinal brush-border membrane vesicles (BBMVs). In the prese
- Fujita, Takuya,Morishita, Yutaka,Ito, Hitomi,Kuribayashi, Daisuke,Yamamoto, Akira,Muranishi, Shozo
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Read Online
- Synthesis of fully Protected Peptides on a Tetraethyleneglycol Diacrylate (TTEGDA)-Crosslinked Polystyrene support with a Photolytically Detachable 2-Nitrobenzyl Anchoring group
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1-Chloromethyl-2-nitro tetraethyleneglycol diacrylate (TTEGDA)-crosslinked polystyrene resin was prepared by nitration of chloromethyl (4percent) TTEGDA-crosslinked polystyrene resin and used as a photosensitive solid support for the preparation of fully
- Renil, M.,Pillai, V. N. Rajasekharan
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Read Online
- Facile Cu(ii)-mediated conjugation of thioesters and thioacids to peptides and proteins under mild conditions
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The bioconjugation of peptide derivatives such as polypeptides, peptide-based probes and proteins is a vibrant area in many scientific fields. However, reports on metal-mediated chemical methods towards native peptides especially non-engineering protein modification under mild conditions are still limited. Herein, we describe a novel Cu(ii)-mediated strategy for the conjugation of thioesters/thioacids to peptides under mild conditions with high functional group tolerance. Based on this strategy, polypeptides, even peptide-based fluorescent probes, can be efficiently constructed. Finally, the selective modification of lysine residues of native Ub with thioesters could be realized and complete conjugation of Ub could be achieved even under equivalent Cu(ii). These promising results could greatly expand Cu(ii)-mediated reaction strategies on chemical biology and molecular imaging.
- Sun, Yao,Lyu, Zhenbin,Wang, Zhiqiang,Zeng, Xiaodong,Zhou, Hui,Xu, Fuchun,Chen, Ziyang,Xu, Yuling,Xu, Ping,Hong, Xuechuan
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supporting information
p. 3610 - 3614
(2018/05/26)
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- Synthesis and conformational characterization of diketopiperazines bearing a benzyl moiety
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Diketopiperazines bearing a benzyl moiety with different para-substituents were synthesized and analyzed by 1HNMR spectroscopy. All of these diketopiperazines were found to adopt a folded conformation according to the upfield chemical shift of the cis-proton (cis to the benzyl moiety) due to a shielding effect in the 1HNMR spectra. An intramolecular CH-π interaction appears to be an important factor for the folded conformation due to the effects of para-substituents on the benzyl group.
- Nakao, Michiyasu,Toriuchi, Yuriko,Fukayama, Shintaro,Sano, Shigeki
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p. 340 - 342
(2014/03/21)
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- Phosphorus oxychloride as an efficient coupling reagent for the synthesis of esters, amides and peptides under mild conditions
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A mild method is described for the conversion of carboxylic acids into esters, amides, as well as peptides without racemization through carboxyl activation by the reagent combination of POCl3 and DMAP. Long chain alcohols could be converted to the corresponding ester in good yields. 31P NMR spectrum was used to detect phosphorus-containing intermediates in ongoing reactions directly, and a possible mechanism has been proposed based on these results. The Royal Society of Chemistry 2013.
- Chen, Hu,Xu, Xunfu,Liu, Liu,Tang, Guo,Zhao, Yufen
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p. 16247 - 16250
(2013/09/23)
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- HMDO-promoted peptide and protein synthesis in ionic liquids
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Hexamethyldisiloxane (HMDO) has been developed to efficiently promote the metal-free direct coupling of an amino function of one cysteine-free peptide or protein and a C-terminal thioester of the second peptide in ionic liquids. The amide-coupling reaction proceeds smoothly under mild conditions to afford the corresponding products in good to excellent yields (63-94%). Peptide couplings were also achieved using in-situ-generated thioesters by the thioesterification of oxo esters.
- Duan, Jianli,Sun, Yao,Chen, Hao,Qiu, Guofu,Zhou, Haibing,Tang, Ting,Deng, Zixin,Hong, Xuechuan
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p. 7013 - 7022
(2013/08/23)
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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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- An efficient protocol for the amidation of carboxylic acids promoted by trimethyl phosphite and iodine
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A practical, one-pot protocol is described for the conversion of carboxylic acids into amides through carboxyl activation by the reagent combination of trimethyl phosphite and iodine. This method integrates several advantages: (1) it allows amines to be chemoselectively acylated with excellent results in the presence of sulfur and oxygen nucleophiles; (2) the method shows wide generality in respect of solvent, base, and substrate; (3) the reagents used are widely available and much less expensive than common coupling reagents, and (4) the process is remarkably convenient, permitting extraction, recrystallization, and column chromatography as optional work-up procedures. The chemoselectivity and generality of the method, the low cost, and wide availability of reagents combined with the ease of use make it a very favorable process.
- Luo, Qun-Li,Lv, Lina,Li, Yu,Tan, Jian-Ping,Nan, Wenhui,Hui, Qun
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supporting information; experimental part
p. 6916 - 6922
(2012/01/06)
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- Stereoselective ring contraction of 2,5-diketopiperazines: An innovative approach to the synthesis of promising bioactive 5-membered scaffolds
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Ring contraction of 2,5-diketopiperazines by TRAL-alkylation led us to the stereoselective synthesis of original pyrrolidine-2,4-diones, a novel series of promising molecules with moderate anti-proliferative activity on breast cancer cells.
- Coursindel, Thibault,Restouin, Audrey,Dewynter, Georges,Martinez, Jean,Collette, Yves,Parrot, Isabelle
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experimental part
p. 210 - 217
(2010/10/01)
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- Catalytic staudinger-vilarrasa reaction for the direct ligation of carboxylic acids and azides
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2,2 -Dipyridyl diselenide (PySeSePy) is the catalyst or activator of choice for the direct reaction of carboxylic acids with azides and trimethylphosphine at room temperature. The mechanism of the process, which is not an aza-Wittig reaction, has been elucidated.
- Bures, Jordi,Martin, Manuel,Urpi, Felix,Vilarrasa, Jaume
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experimental part
p. 2203 - 2206
(2009/08/07)
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- Microwave-assisted synthesis of 2,5-piperazinediones under solvent-free conditions
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A general, efficient and environmentally friendly procedure for the synthesis of 2,5-piperazinediones is described, involving the microwave irradiation of N-Boc dipeptide esters. Georg Thieme Verlag Stuttgart.
- Lopez-Cobenas, Alberto,Cledera, Pilar,Sanchez, J. Domingo,Lopez-Alvarado, Pilar,Ramos, M. Teresa,Avendano, Carmen,Menendez, J. Carlos
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p. 3412 - 3422
(2007/10/03)
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- A rapid and efficient synthesis of β-casomorphin employing Boc-amino acids and 9-fluorenylmethyl chloroformate as a coupling agent
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The synthesis of β-casomorphin H-Tyr-Pro-Phe-Pro-Gly-OH employing Boc group for Nα-protection and 9-fluorenylmethyl chloroformate (Fmoc-Cl) for the formation of peptide bond is described. The protocol employing Fmoc-Cl as coupling reagent is found to be simple, efficient and rapid. All the intermediate peptides as well as the final protected peptide Boc-Tyr( iBu)-Pro-Phe-Pro-Gly-OMe have been isolated and fully characterized. They have been obtained in good yield and with high purity.
- Babu, V.V. Suresh,Tantry
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p. 2708 - 2712
(2007/10/03)
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- Condensation of α-Amino Acid with Amine in the Absence of a Coupling Agent
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Treatment of N-(4-nitrophenoxycarbonyl)amino acid with an equimolar amount of amine in the absence of a coupling agent gave the corresponding α-amino acid amide in high yield.
- Yamaguchi, Jun-Ichi,Nagai, Shinya,Fukuoka, Emi,Suyama, Takayuki
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p. 830 - 831
(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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- Inhibition of urease activity by dipeptidyl hydroxamic acids
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A series of dipeptidyl hydroxamic acids (H-X-Gly-NHOH: X = amino acid residues) was synthesized, and the inhibitory activity against Jack bean and.Proteus mirabilis ureases [EC 3.5.1.5] was examined. A number of H-X-Gly-NHOH inhibited Jack bean urease wit
- Odake,Nakahashi,Morikawa,Takebe,Kobashi
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p. 2764 - 2768
(2007/10/02)
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- BroP: A new reagent for coupling N-methylated amino acids
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BroP (bromo tris(dimethylamino) phosphonium hexafluorophosphate) is a particularly suitable reagent for coupling N-methylated amino acids. It is stable and gives very high yields in short reaction times. Dipeptides are obtained without appreciable epimeri
- Coste,Dufour,Pantaloni,Castro
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p. 669 - 672
(2007/10/02)
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- (Trimethylsilyl)ethoxyacetylene. An Effective Reagent for Mild Dehydrative Condensation of Carboxylic Acids and H-Acidic Materials
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(Trimethylsilyl)ethoxyacetylene, a stable and easy to handle dehydrating reagent, is quite effective for the title condensation to prepare ester-, lactone-, lactam-, and peptide-linkages under mild conditions.
- Kita, Yasuyuki,Akai, Shuji,Yamamoto, Miki,Taniguchi, Miyako,Tamura, Yasumitsu
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p. 334 - 337
(2007/10/02)
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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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- 2-Pyridon-1-yl Diphenyl Phosphate. A Useful New Reagent for the Synthesis of Amides and Peptides
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2-Pyridon-1-yl diphenyl phosphate is found to be a useful coupling agent for the synthesis of amides and practically racemization-free peptides.
- Kim, Sunggak,Kim, Sung Soo
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- 3,3'-(Phenylphosphinylidene)bis and 3,3'-(Phenylphosphinylidene)bis. New Activating Agents
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New activating agents, 3,3'-(phenylphophinylidene)bis (4) and 3,3'-(phenylphosphinylidene)bis (5), were readily prepared by the reaction of phenylphosphonic dichloride (3) with 2(3H)-benzoxazolone (1) and 2(3H)-benzothiazolone (2) respectively in the presence of triethylamine at room temperature.The new activating agents 4 and 5 were found to be useful for the preparation of amides, esters, and dipeptides under mild conditions.Furthemore, the direct polycondensation of isophthalic acid with aromatic diamines using the activating agent 4 in the presence of pyridine proceeded fast at room temperature to produce polyamides with inherent viscosities up to 0.80 dL/g.
- Ueda, Mitsuru,Mochizuki, Amane,Hiratsuka, Ichiro,Oikawa, Hideaki
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p. 3291 - 3297
(2007/10/02)
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- 1,2-Benzisoxazol-3-yl Diphenyl Phosphate: A New, Reactive Activating Agent for the Synthesis of Amides, Esters, and Peptides via Condensation
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A new activating agent for condensations, 1,2-benzisoxazol-3-yl diphenyl phosphate (1), was readily prepared in high yield by the reaction of 1,2-benzisoxazol-3-ol (2) with diphenyl phosphorochloridate (3) in the presence of triethylamine in benzene.The reaction of the carboxylic acids with the amines in the presence of 1 was investigated by two procedures, a two-step method and a one-step procedure.Both methods gave the corresponding amides and esters in high yields under mild conditions, but the one-step procedure was found to be superior to the two-step procedure because of its simplicity and speed.Furthermore, the activating agent 1 was shown to be a useful peptide forming reagent.
- Ueda, Mitsuru,Oikawa, Hideaki
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p. 760 - 763
(2007/10/02)
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- 2-HALOVINYL ARYL SULFONES: NEW COUPLING REAGENTS FOR CARBOXAMIDE FORMATION
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E-2-Chlorovinyl p-nitrophenyl sulfone 6 and 2-bromo-2-trifluoromethylvinyl phenyl sulfone 7a reacted with carboxylic acids in the presence of a molar equiv of Et3N affording the corresponding 2-acyloxyvinyl sulfones 8, 11, 17, 18, 22, 25, 28 and 29.The latter, on treatment with amines, gave amides 9, 13, 19, 23 and 26 and peptides 30 and 32.These reagents 6 and 7a were also used for the formation of N-methylanilides 13d, 13e, 19d, 23 and 26.Particularly, 6 was successfully used for synthesis of a macrocyclic lactam 23 involving a N-methylanilide moiety.The amidation reac tions proceeded under essentially neutral conditions.Therefore, base-sensitive β-hydroxycarboxy-N-methylanilides such as 26, whose structural unit was involved in maytansine 5, could be prepared by the present method.The reagent 6 was also effective for the preparation of peptides such as Val-N-MeVal derivatives (e.g.32), which were difficult to prepare by other methods.
- Shimagaki, Masayuki,Koshiji, Hiroko,Oishi, Takeshi
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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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- 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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- SYNTHESIS OF PENTAPEPTIDES RELATED BOTH TO SUBSTANCE P C-TERMINAL FRAGMENT AND MET-ENKEPHALIN
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Six pentapeptide amides related both to Substance P C-terminal fragment and to Met-enkephalin have been synthesized.Syntheses were effected by coupling fragments 3 + 2 in solution.The DCC + HOBt method was used for synthesis of peptide fragments and final
- Lipkowski, Andrzej W.,Misicka, Aleksandra,Drabarek, Stefania
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p. 813 - 818
(2007/10/02)
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