- Convenient synthesis of C-terminal di- and tri-peptide amides from N-protected dipeptidoylbenzotriazoles
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N-Protected dipeptidoylbenzotriazoles react with aqueous ammonia to give dipeptide primary amides (77-98%) and with N-unprotected α-amino amides to afford tripeptide primary amides (82-86%).
- Celik, Ilhami,Abdel-Fattah, Ashraf A.A.
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experimental part
p. 4923 - 4929
(2009/10/09)
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- The efficient preparation of di- and tripeptides by coupling N-(Cbz- or Fmoc-α-aminoacyl)benzotriazoles with unprotected amino acids
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N-(Cbz- or Fmoc-α-aminoacyl)benzotriazoles 2 and N-protected peptidoylbenzotriazoles 6 are coupled in aqueous acetonitrile solution with free amino acids or dipeptides to prepare: (i) 22 chirally pure dipeptides 5a-v (in an average yield of 82%) from N-(Cbz- or Fmoc-α-aminoacyl)benzotriazoles 2 and unprotected amino acids, (ii) five chiral tripeptides 7a-e (in an average yield of 75%) from N-protected peptidoylbenzotriazoles 6 and unprotected amino acids, (iii) one chiral tripeptide 7g (62%) from N-(Cbz- or Fmoc-α- aminoacyl)benzotriazole 2a and the free dipeptide 8. In all, N-(Cbz- or Fmoc-α-aminoacyl)benzotriazole derivatives of 17 of the 20 naturally occurring amino acids were used, including those containing the following unprotected side chain functionalities: alcoholic -OH (Ser), indole -NH (Trp), imidazole -NH, phenolic -OH (Tyr), -CONH2 (Gln, Asn), -SH (Cys), -CO2H (Glu, Asp), and -S-S (Cystine). Support for the complete retention of chirality was obtained by parallel experiments involving D-Ala, L-Ala, and DL-Ala for the preparation of di- and tripeptides. This and other evidence for chiral integrity was supported by NMR and HPLC analyses. Georg Thieme Verlag Stuttgart.
- Katritzky, Alan R.,Angrish, Parul,Suzuki, Kazuyuki
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p. 411 - 424
(2007/10/03)
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- TREATMENT OF PROTEIN FOLDING DISORDERS
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In certain embodiments, the invention is directed to a method for treating a protein folding disorder such as Alzheimer's disease, dementia, Parkinson's disease, Huntington's disease and prion-based spongiform encephalopathy. The method comprises the administration to a subject of a compound of the formula (I) wherein A and B are independently a mono- or bicyclic aromatic group or heteroaromatic cyclic group. In preferred embodiments, the compounds are bis-indole compounds.
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Page/Page column 128-129
(2010/11/25)
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- STEREOSELECTIVITY IN MICELLAR AND VESICULAR REACTIONS
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The diastereoselectivity of esterolytic cleavage of certain dipeptide and tripeptide activated esters is lower in thio-functionalized vesicles than in comparable micelles.This is thought to be a mechanism-specific effect related to the greater molecular o
- Moss, Robert A.,Taguchi, Takayuki,Bizzigotti, George O.
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p. 1985 - 1988
(2007/10/02)
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