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A new synthetic route to tert-butyloxycarbonylaminoacyl-4-(oxymethyl)phenylacetamidomethyl-resin, an improved support for solid-phase peptide synthesis
Abstract
The preferred route to the aminoacylated 4-(oxymethyl)phenylacetamidomethyl-resin (-0CH2-Pam-resin) in-volves the condensation of a Boc-aminoacyl-4-(oxymethyl)phenylacetic acid (Boc = tert-butyloxycarbonyl) with aminomethyl-resin. Aminomethyl-resin was synthesized by direct amidoalkylation of polystyrene resin to give the phthalimidomethyl-resin. The extent of reaction was monitored by IR, allowing the reaction to be stopped at any chosen level of substitution. Hydrazinolysis gave aminomethyl-resin. The Boc-amino acid was converted in solution to a substituted benzyl ester by reaction with 4-(bromomethyl)phenylacetic acid phenacyl ester. Zinc-acetic acid reduction removed the phenacyl group to give the Boc-aminoacyl-4-(oxymethyl)phenylacetic acid, which was cou-pled to aminomethyl-resin with DCC. The benzyl ester bond of the resulting aminoacyl-OCH2-Pam-resins was ap-proximately 100-fold more stable in refluxing trifluoroacetic acid than the aminoacyl-0CH2-resin. Comparison with a solution analogue showed that this was due to the inductive effect of the p-acetamidomethyl group. Cleavage yields (HF-anisole, 9:l v/v, 30 min, 0 "C) were 82-100 % for the aminoacyl- and peptidyl-OCH2-Pam-resins exam-ined. The aminoacyl-OCH2-Pam-resins showed resistance to primary amine nucleophiles similar to that of the ami-noacyl-OCH2-resin. No racemization (
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Citations
Cited by
Linkers 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
Humphries, M. J., Akiyama, S. K., Komoriya, A., Olden, K., & Yamada, K. M. (1986) · The Journal of cell biology · doi:10.1083/jcb.103.6.2637 · Cited by 438
Solid Phase Synthesis of Polyamides Containing Imidazole and Pyrrole Amino Acids
Baird, E. E., & Dervan, P. B. (1996) · Journal of the American Chemical Society · doi:10.1021/ja960720z · Cited by 360
Humphries, M. J., Komoriya, A., Akiyama, S. K., Olden, K., & Yamada, K. M. (1987) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)48327-5 · Cited by 347
Pentelute, B. L., Gates, Z. P., Dashnau, J. L., Vanderkooi, J. M., & Kent, S. B. H. (2008) · Journal of the American Chemical Society · doi:10.1021/ja801352j · Cited by 77
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Metadata
- Authors
- Mitchell, A. R., Kent, S. B. H., Engelhard, M., & Merrifield, R. B.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1978-07
- Volume
- 43
- Issue
- 14
- Pages
- 2845-2852
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2003867383
- Cited by
- 326
- References
- 0
- FWCI
- 3.94
- Type
- journal article
- Language
- en
- Open access
- closed
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- Mitchell, A. R., Kent, S. B. H., Engelhard, M., & Merrifield, R. B. (1978). A new synthetic route to tert-butyloxycarbonylaminoacyl-4-(oxymethyl)phenylacetamidomethyl-resin, an improved support for solid-phase peptide synthesis. The Journal of Organic Chemistry. https://doi.org/10.1021/jo00408a022
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