NDLI: The Efficient Preparation of Di- and Tripeptides by CouplingN-(Cbz- or Fmoc-α-aminoacyl)benzotriazoles with Unprotected Amino Acids

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The Efficient Preparation of Di- and Tripeptides by CouplingN-(Cbz- or Fmoc-α-aminoacyl)benzotriazoles with Unprotected Amino Acids

Content Provider	Scilit
Author	Katritzky, Alan R. Angrish, Parul Suzuki, Kazuyuki
Copyright Year	2006
Description	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), $-CONH_{2}$ (Gln, Asn), -SH (Cys), $-CO_{2}$H (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.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2006-926287.pdf
Ending Page	424
Page Count	14
Starting Page	411
ISSN	00397881
e-ISSN	1437210X
DOI	10.1055/s-2006-926287
Journal	Synthesis
Issue Number	3
Volume Number	2006
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2006-01-11
Access Restriction	Open
Subject Keyword	Journal: Synthesis Organic Chemistry N-(protected Α-aminoacyl)benzotriazole Acylating Reagent N-cbz-peptidoylbenzotriazole
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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The Efficient Preparation of Di- and Tripeptides by Coupling N-(Cbz- or Fmoc-a-aminoacyl)benzotriazoles with Unprotected Amino Acids Coupling of N-(Cbz- or Fmoc-a-aminoacyl)benzotriazoles with Unprotected Amino Acids

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