2537-91-9Relevant articles and documents
Ecological base-conditioned preparation of dipeptides using unprotected α-amino acids containing hydrophilic side chains
Ezawa, Tetsuya,Jung, Seunghee,Kawashima, Yuya,Noguchi, Takuya,Imai, Nobuyuki
, p. 689 - 696 (2017/07/22)
The coupling reactions of 3-phenylpropanoic acid and Ncarboxybenzyl á-amino acids with unprotected á-amino acids containing hydrophilic side chains such as aliphatic alcohol, aromatic alcohol, thiol, carboxylic acid, and amide afforded the corresponding amides in 6696% yield without racemization via the corresponding mixed carbonic carboxylic anhydrides under basic conditions through an ecological green synthetic method.
α-N-Protected dipeptide acids: A simple and efficient synthesis via the easily accessible mixed anhydride method using free amino acids in DMSO and tetrabutylammonium hydroxide
Verardo,Gorassini
, p. 315 - 324 (2013/06/05)
The importance of dipeptides both in medicinal and pharmacological fields is well documented and many efforts have been made to find simple and efficient methods for their synthesis. For this reason, we have investigated the synthesis of α-N-protected dipeptide acids by reacting the easily accessible mixed anhydride of α-N-protected amino acids with free amino acids under different reaction conditions. The combination of TBA-OH and DMSO has been found to be the best to overcome the low solubility of amino acids in organic solvents. Under these experimental conditions, the homogeneous phase condensation reaction occurs rapidly and without detectable epimerization. The present method is also applicable to side-chain unprotected Tyr, Trp, Glu, and Asp but not Lys. This latter residue is able to engage two molecules of mixed anhydride giving the corresponding isotripeptide. Moreover, the applicability of this protocol for the synthesis of tri- and tetrapeptides has been tested. This approach reduces the need for protecting groups, is cost effective, scalable, and yields dipeptide acids that can be used as building blocks in the synthesis of larger peptides.
Pharmaceutical composition having an excellent absorption property
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, (2008/06/13)
A compound represented by the formula: STR1 wherein R1 is a hydrogen atom, a fluorine atom, a nitro group, a hydroxyl group or a hydroxyl group protected by an esterifying group; X is CO or SO2 ; --Y-- is a straight bond, a lower alkylene group, a substituted or unsubstituted vinylene group, or group having the formula --CH2 --O-- or --O--CH2 --; R2 is a substituted or unsubstituted phenyl or naphthyl group, or R2 --Y--CO is N-benzyloxycarbonylphenylalanyl, N-benzyloxycarbonyl-4-fluorophenylalanyl or N-(m-methoxycinnamoyl)-phenylalanyl group; or a non-toxic salt thereof is disclosed along with pharmaceutical compositions containing these compounds and methods of using these compositions to increase the rate of absorption of medicines.