Macrocyclic triamines as linkers in two-armed receptors for peptides

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 22, 1996, Pages 2673-2676

  Iorio, Edward James ^a   Still, W Clark ^a  

^a Columbia University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG RECEPTOR; MACROCYCLIC COMPOUND;

AMINO ACID COMPOSITION; ARTICLE; DRUG SYNTHESIS; PROTEIN BINDING; STRUCTURE ACTIVITY RELATION;

EID: 0030593884     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00500-8     Document Type: Article

References (13)

1. 1. Review: Still, W.C. Accnts. Chem. Res. 1996, 29, 155. See also: Maletic, M.; Wennemers, H.; McDonald, D.Q.; Breslow, R.C.; Still, W.C. Angew. Chem. Int. Ed. Engl. 1996, 35, 1490.
2. 1. Review: Still, W.C. Accnts. Chem. Res. 1996, 29, 155. See also: Maletic, M.; Wennemers, H.; McDonald, D.Q.; Breslow, R.C.; Still, W.C. Angew. Chem. Int. Ed. Engl. 1996, 35, 1490.
3. 2. a) Wennemers, H.; Yoon, S.S.; Still, W.C. J. Org. Chem. 1995, 60, 1108;
4. b) Shao, Y.; Still, W.C. J. Org. Chem. 1996, 61, 6086.
5. 3. a) Boyce, R.; Li, G.; Nestler, H.P.; Suenega, T.; Still, W.C. J. Am. Chem. Soc. 1994, 116, 7955;
6. b) LaBrenz, S.R.; Kelly, J.W. J. Am. Chem. Soc. 1995, 117, 1655;
7. c) Gennari, C.; Nestler, H.P.; Salom, B.; Still, W.C. Angew. Chem. Intl. Ed. Engl. 1995, 34, 1765;
8. d) Burger, M.T.; Still, W.C. J. Org. Chem. 1995, 60, 7382;
9. e) Cheng, Y.; Suenaga, T.; Still, W.C. J. Am. Chem. Soc. 1996, 118, 1813.
10. 4. Kovacs, Z.; Sherry, A.D. Tetrahedron Lett. 1995, 36, 9269.
11. 5. This solid phase assay has been described previously: Yoon, S.S.; Still, W.C. Tetrahedron 1994, 51, 567. AAn = Gly, (D and L) Ala, Val, Pro, Ser(O-tBu), Asn(N-trityl), Gln(N-trityl), Lys(N-Boc).
12. 6. Ohlmeyer, M.H.J.; Swanson, R.N.; Dillard, L.W.; Reader, J.C.; Asouline, G.; Kobayashi, R.; Wigler, M.; Still, W.C. Proc. Natl. Acad. Sci. USA 1993, 90, 10922.
13. 7. For technical reasons, the deprotected tripeptide library was not N-acetylated but instead was N-acylated with a variety of simple organic acylating agents (listed in ref 5). In our binding assays here, virtually no selectivity for the N-acyl group was observed.