3005-87-6Relevant academic research and scientific papers
Tandem deprotection/coupling for peptide synthesis in water at room temperature
Cortes-Clerget, Margery,Berthon, Jean-Yves,Krolikiewicz-Renimel, Isabelle,Chaisemartin, Laurent,Lipshutz, Bruce H.
supporting information, p. 4263 - 4267 (2017/09/28)
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.
Metalloporphyrin receptors for histidine-containing peptides
Liu, Hui,Li, Zhan-Ting
supporting information, p. 659 - 662 (2014/06/09)
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.
Synthesis of dipeptides from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione activated α-amino acids
Nowshuddin, Shaik,Ram Reddy
scheme or table, p. 22 - 25 (2011/04/18)
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.
Bromelain catalyzed synthesis of peptides in organic solvent
Tai, Dar-Fu,Fu, Shu-Lin
, p. 179 - 183 (2007/10/03)
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.
New system for peptide synthesis using N-acylpyrazoles
Kashima, Choji,Tsuruoka, Shiro,Mizuhara, Saori
, p. 413 - 424 (2007/10/03)
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.
Preparation of carboxamides via carboxylic-phosphoric anhydrides
Gaede, Bruce
, p. 92 - 93 (2013/09/08)
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.
Rapid, one-pot synthesis of urethane-protected tripeptides
Zhu, Yun-Fei,Fuller, William D.
, p. 807 - 810 (2007/10/02)
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.
Enol esters as intermediates for the facile conversion of amino acids into amides and dipeptides
Kabouche,Bruneau,Dixneuf
, p. 5359 - 5362 (2007/10/02)
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.
KINETICS OF THE ALKALINE HYDROLYSIS OF SEVERAL N-BENZYLOXYCARBONYLDIPEPTIDE METHYL AND ETHYL ESTERS
Hoogwater, D. A.,Peereboom, M.
, p. 5325 - 5332 (2007/10/02)
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.
