The DOI matches its Crossref record; 15 of the 15 references it cites were found in a registry or an index.
Backbone Amide Linker (BAL) Strategy for Solid-Phase Synthesis of C-Terminal-Modified and Cyclic Peptides1,2,3
Abstract
Peptide targets for synthesis are often desired with C-terminal end groups other than the more usual acid and amide functionalities. Relatively few routes exist for synthesis of C-terminal-modified peptides including cyclic peptides by either solution or solid-phase methods, and known routes are often limited in terms of ease and generality. We describe here a novel B ackbone A mide L inker (BAL) approach, whereby the growing peptide is anchored through a backbone nitrogen, thus allowing considerable flexibility in management of the termini. Initial efforts on BAL have adapted the chemistry of the tris(alkoxy)benzylamide system exploited previously with PAL anchors. Aldehyde precursors to PAL, e.g. 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid, were reductively coupled to the α-amine of the prospective C-terminal amino acid, which was blocked as a tert -butyl, allyl, or methyl ester, or to the appropriately protected C-terminal-modified amino acid derivative. These reductive aminations were carried out either in solution or on the solid phase, and occurred without racemization. The secondary amine intermediates resulting from solution amination were converted to the 9-fluorenylmethoxycarbonyl (Fmoc)-protected preformed handle derivatives, which were then attached to poly(ethylene glycol)−polystyrene (PEG-PS) graft or copoly(styrene−1% divinylbenzene) (PS) supports and used to assemble peptides by standard Fmoc solid-phase chemistry. Alternatively, BAL anchors formed by on-resin reductive amination were applied directly. Conditions were optimized to achieve near-quantitative acylation at the difficult step to introduce the penultimate residue, and a side reaction involving diketopiperazine formation under some circumstances was prevented by a modified protocol for N α -protection of the second residue/introduction of the third residue. Examples are provided for the syntheses in high yields and purities of representative peptide acids, alcohols, N,N -dialkylamides, aldehydes, esters, and head-to-tail cyclic peptides. These methodologies avoid postsynthetic solution-phase transformations and are ripe for further extension.
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Citations
Cites
Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides
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Solid‐phase peptide synthesis: a silver anniversary report*
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Synthesis of ‘head-to-tail’ cyclized peptides on solid support by Fmoc chemistry
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Reverse anomeric effect and the synthesis of a-glycosides
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Cited by
Peptide Coupling Reagents, More than a Letter Soup
El-Faham, A., & Albericio, F. (2011) · Chemical Reviews · doi:10.1021/cr100048w · Cited by 1,245
Isidro-Llobet, A., Álvarez, M., & Albericio, F. (2009) · Chemical Reviews · doi:10.1021/cr800323s · Cited by 850
Self-citationLinkers and Cleavage Strategies in Solid-Phase Organic Synthesis and Combinatorial Chemistry
Guillier, F., Orain, D., & Bradley, M. (2000) · Chemical Reviews · doi:10.1021/cr980040+ · Cited by 516
Solid‐phase peptide synthesis using acetonitrile as a solvent in combination with PEG‐based resins
Acosta, G. A., del Fresno, M., Paradis‐Bas, M., Rigau‐DeLlobet, M., Côté, S., Royo, M., & Albericio, F. (2009) · Journal of Peptide Science · doi:10.1002/psc.1158 · Cited by 63
Self-citation(2000) · doi:10.1002/1097-0282(2000)55:2<123::aid-bip30>3.0.co;2-f
Metadata
- Authors
- Jensen, K. J., Alsina, J., Songster, M. F., Vágner, J., Albericio, F., & Barany, G.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1998-05-19
- Volume
- 120
- Issue
- 22
- Pages
- 5441-5452
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2084631067
- Cited by
- 277
- References
- 15
- FWCI
- 5.74
- Type
- journal article
- Language
- en
- Open access
- closed
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