21285-27-8Relevant articles and documents
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.
Efficient peptide coupling involving sterically hindered amino acids
Katritzky, Alan R.,Todadze, Ekaterina,Angrish, Parul,Draghici, Bogdan
, p. 5794 - 5801 (2008/02/09)
(Chemical Equation Presented) Hindered amino acids have been introduced into peptide chains by coupling N-(Cbz- and Fmoc-α-aminoacyl) benzotriazoles with amino acids, wherein at least one of the components was sterically hindered, to provide compounds 3a-e, (3c +3 c′), 5a-d, (5a + 5a′), 6a-c, (6b + 6b′), 8a-c, 9a-e, 10a-d, and (10a + 10a′) in isolated yields of 41-95% with complete retention of chirality as evidenced by NMR and HPLC analysis. The benzotriazole activation methodology is a new route for the synthesis of sterically hindered peptides. (Note: compound numbers written within brackets represent diastereomeric mixtures or racemates; compound numbers without brackets represent enantiomers.)
Peptides influencing diuresis and natriuresis, a process for their preparation, agents containing them, and their use
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, (2008/06/13)
The invention relates to peptides of the formula in which RN denotes an acyl radical, L denotes a radical of a lipophilic, neutral α-amino acid, N denotes a radical of an neutral α-amino acid, B2 denotes the radical of a basic α-amino acid, and RC denotes an amido radical; a process for their preparation, agents containing these peptides, and their use.