Abstract
Synthetic approaches to gabapentin bioconjugates that overcome the tendency of gabapentin to cyclize into its γ-lactam are studied. Gabapentin was converted by N-acylation at its N-terminus into di-, tri-, and tetrapeptides (L-Ala-Gbp, L-Val-Gbp, L-Ala-L-Phe-Gbp, Gly-L-Ala-β-Ala-Gbp). Carboxyl-activated Boc-protected gabapentin was used to N-, O-, and S-acylate small peptides and hormones to give conjugates that could also provide prodrugs containing conformationally constrained gabapentin units.
Original language | English (US) |
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Pages (from-to) | 1479-1486 |
Number of pages | 8 |
Journal | Bioorganic and Medicinal Chemistry |
Volume | 22 |
Issue number | 4 |
DOIs | |
State | Published - Feb 15 2014 |
Externally published | Yes |
Keywords
- Benzotriazole
- Coupling
- Cyclization
- Gabapentin
- Peptide
ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry