2562-48-3Relevant articles and documents
Postsynthetic Modification of Phenylalanine Containing Peptides by C-H Functionalization
Terrey, Myles J.,Perry, Carole C.,Cross, Warren B.
, p. 104 - 108 (2019/01/11)
New methods for peptide modification are in high demand in drug discovery, chemical biology, and materials chemistry; methods that modify natural peptides are particularly attractive. A Pd-catalyzed, C-H functionalization protocol for the olefination of phenylalanine residues in peptides is reported, which is compatible with common amino acid protecting groups, and the scope of the styrene reaction partner is broad. Bidentate coordination of the peptide to the catalyst appears crucial for the success of the reaction.
Oxidative damage of aromatic dipeptides by the environmental oxidants NO2 and O3
Gamon,White,Wille
, p. 8280 - 8287 (2015/01/08)
Irreversible oxidative damage at both aromatic side chains and dipeptide linkage occurs in the aromatic N- and C-protected dipeptides 7-11 upon exposure to the environmental pollutants NO2 and O3. The reaction proceeds through initial oxidation of the aromatic ring by in situ generated NO3, or by NO2, respectively, which leads to formation of nitroaromatic products. The indole ring in Phe-Trp undergoes oxidative cyclization to a pyrroloindoline. An important reaction pathway for dipeptides with less oxidisable aromatic side chains proceeds through fragmentation of the peptide bond with concomitant acyl migration. This process is likely initiated by an ionic reaction of the amide nitrogen with the NO2 dimer, N2O4. This journal is
A traceless approach to amide and peptide construction from thioacids and dithiocarbamate-terminal amines
Chen, Wenteng,Shao, Jiaan,Hu, Miao,Yu, Wanwan,Giulianotti, Marc A.,Houghten, Richard A.,Yu, Yongping
, p. 970 - 976 (2013/06/05)
A novel and traceless strategy has been devised that allows a coupling of thioacids and dithiocarbamate-terminal amines. This strategy had been assumed to be dependent on the attachment of a functional equivalent of a cysteine side chain in earlier native chemical ligation approaches. This approach enables the traceless removal of CS2 to directly generate the desired amide bond and is compatible with a range of unprotected side chains of amino acid. The ability to produce amide or peptides by a traceless removal of the auxiliary is a significant virtue of the method. Meanwhile, the application of this new peptide-bond-forming reaction to the synthesis of novel endomorphin (EM) derivatives with various binding potencies was realized.
Direct amidation of amino acid derivatives catalyzed by arylboronic acids: Applications in dipeptide synthesis
Liu, Shouxin,Yang, Yihua,Liu, Xinwei,Ferdousi, Farhana K.,Batsanov, Andrei S.,Whiting, Andrew
, p. 5692 - 5700 (2013/09/12)
The direct amidation of amino acid derivatives catalyzed by arylboronic acids has been examined. The reaction was generally slow relative to simple amine-carboxylic acid combinations though proceeded at 65-68 °C generally avoiding racemization. 3,4,5-Trifluorophenylboronic and o-nitrophenylboronic acids were found to be the best catalysts, though for slower dipeptide formations, high catalyst loadings were required and an interesting synergistic catalytic effect between two arylboronic acids was discovered. Arylboronic acids can be used to catalyze the direct amide formation of protected amino acid derivatives. For less reactive amino acids, cooperative catalysis can be used involving two arylboronic acids, one electron-rich and one electron-deficient, at high catalyst loadings to give good conversions at moderate temperatures. Copyright
METHOD FOR STORING QUATERNARY AMMONIUM SALT
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Page 27, 28, (2008/06/13)
A method of improving the stability of a quaternary ammonium salt and a method of efficiently preparing the quaternary ammonium salt having improved stability.
Phenylalanine racemization: A side reaction of dipeptide formation
Kotlova,Timokhina,Chestukhina,Stepanov
, p. 579 - 583 (2007/10/03)
It was shown that acetylated dipeptides, Ac-D-Phe-D-Phe-OH, Ac-L-Phe-L-Phe-OH, Ac-D-Phe-L-Phe-OH, and Ac-L-Phe-D-Phe-OH, are formed during D-phenylalanine racemization. The overall content of these dipeptides in the reaction mixture ranged from 40 to 60% depending on the reaction conditions. We concluded that, like α-aminoisobutyric acid, phenylalanine is prone to polymerization under racemization conditions.
Intermolecular β-sheet stabilization with aminopyrazoles
Kirsten, Christian N.,Schrader, Thomas H.
, p. 12061 - 12068 (2007/10/03)
3-Aminopyrazole derivatives are the first artificial templates that stabilize the β-sheet conformation in N/C-protected dipeptides by purely intermolecular interactions. In the complex two aminopyrazole molecules lie exactly above and below the peptide ba
Electrostatic interaction and induced fitting of the rhodium(I) complex coordinated by diphosphine ligand having an amino group in the diastereoselective hydrogenation of dehydrodipeptides
Yamada, Issaku,Fukui, Kouta,Aoki, Yoshihiro,Ikeda, Satoru,Yamaguchi, Motowo,Yamagishi, Takamichi
, p. 115 - 120 (2007/10/03)
Rhodium(I)-[2-[2-(dimethylamino)ethyl]-1,3-propanediyl]bis(diphenylphosphine) (DPP-AE) catalyst achieved an effective 1,4-asymmetric induction and afforded high diastereoselectivity (max. 96% d.e.) in the hydrogenation of dehydrodipeptides in protic solve
Tandem asymmetric syntheses from achiral precursors. Asymmetric homogeneous reduction of bisdehydrodipeptides
Baba, Sana El,Sartor, Karina,Poulin, Jean-Claude,Kagan, Henri B.
, p. 525 - 533 (2007/10/02)
Sequential asymmetric syntheses on an achiral substrate with two prochiral centers is a direct route to products with two asymmetric centers.The product distribution is discussed as a function of the various stereoselectivities.After a general presentation of double asymmetric syntheses, the specific case of asymmetric hydrogenation of some achiral bisdehydrodipeptides is considered.When the chiral ligand of the rhodium catalyst was dipamp, very high diastereoselectivities and enanatioselectivities with respect to resulting dipeptides could be achieved. bisdehydrodipeptides / dipeptides / diop / dipamp / bppm / two sequential asymmetric syntheses / stereoselective hydrogenation / enantioselectivity / diastereoselectivity
ASYMMETRIC SYNTHESIS OF AMINO ACIDS VIA THE CATALYTIC REDUCTION OF SUBSTITUTED ACYLAMINOACRYLIC ACID AZLACTONES. 26. AMINOLYSIS OF 2-METHYL-4-BENZYLOXAZOLIN-5-ONE UPON REACTION WITH S-PHENYLALANINE DERIVATIVES
Lyubeznova, M. R.,Karpeiskaya, E. I.,Klabunovskii, E. I.,Koreshkov, Yu. D.,Lutsenko, A. I.,Lubuzh, E. D.
, p. 731 - 737 (2007/10/02)
The kinetics of aminolysis and racemization of 2-methyl-4-benzyloxazolin-5-one upon reaction with S-phenylalanine methyl ester have been studied in dimethoxyethane solvent.The rates of aminolysis and racemization are comparable.Addition of an achiral component, namely Et3N, to the reaction mixture, however, dramatically increases the rate of racemization.The presence of Et3N also increases the ratio of rate constants for the formation of RS- and SS-diastereomers, which determines the reaction stereoselectivity.
