✦ LIBER ✦
Solid-phase synthesis of peptide–heterocycle hybrids containing a tripeptide-derived 6,6-fused bicyclic subunit
✍ Scribed by Wayne D Kohn; Lianshan Zhang
- Book ID
- 104230824
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 104 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The solid-phase synthesis of peptides incorporating a tripeptide-derived 6,6-fused bicyclic subunit is described. The bicyclic moiety (3,8,10-trisubstituted 2,9-dioxo-5-thia-1,8-diazabicyclo[4.4.0]decane) can be incorporated anywhere in a peptide sequence and is formed spontaneously upon TFA cleavage through condensation of an aldehyde with a backbone amide nitrogen and side-chain thiol, resulting in a thiazinone ring. The reaction is regio-and stereoselective and also allows for the incorporation of the bicyclic moiety, which may represent a constrained b-turn mimic, into a macrocyclic peptide.