Solid-phase synthesis of trisubstituted bicyclic guanidines via cyclization of reduced N-acylated dipeptides

Journal of Organic Chemistry

Volumn 63, Issue 24, 1998, Pages 8622-8623

  Ostresh, John M ^a   Schoner, Christa C ^a   Hamashin, Vince T ^a   Nefzi, Adel ^a   Meyer, Jean Philippe ^a   Houghten, Richard A ^a  

^a TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDE; GUANIDINE DERIVATIVE; POLYAMINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0031767227     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9810617     Document Type: Article

References (19)

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16. Polyamines can be cleaved from the methylbenzhydrylamine linker with HF at 0 °C for 9 h. This compares to the normal 1-1.5 h cleavage of peptide amides. The bicyclic guanidines were also cleaved with HF for 9 h at 0 °C to avoid further experimentation. However, cleavage of several model compounds using 100% TFA for 30 min at room temperature gave 30-50% yields. This demonstrated the positively charged resin-bound bicyclic guanidines could be cleared under much more mild conditions with further experimentation.
17. Ostresh, J. M.; Hamashin, V. T.; Husar, G. M.; Dörner, B.; Houghten, R. A. In Peptides 94: Proceedings of the 23rd European Peptide Symposium; Maia, H. L. S., Ed.; ESCOM: Leiden, 1995; pp 416-417.
18. A variation of the reported method was used in which the relative incorporation of the building blocks was quantitated by RP-HPLC.
19. Blondelle, S.; Crooks, E.; Ostresh, J. M.; Houghten, R. A. Antimicrob. Agents Chemother. 1998, in press.