Mechanistic Insight into the Lability of the Benzyloxycarbonyl (Z) Group inN-Protected Peptides under Mild Basic Conditions
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Other documents of the author: Tena Solsona, Marta; Angulo-Pachón, César A.; Escuder, Beatriu; Miravet, Juan
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comunitat-uji-handle2:10234/7053
comunitat-uji-handle3:10234/8639
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Title
Mechanistic Insight into the Lability of the Benzyloxycarbonyl (Z) Group inN-Protected Peptides under Mild Basic ConditionsDate
2014Publisher
Wiley Online LibraryISSN
1099-0690Type
info:eu-repo/semantics/articleSubject
Abstract
The unexpected lability of Z protecting group under mild basic conditions at room temperature is explained by a mechanism based on anchimeric assistance. It is found that the vicinal amide group stabilizes the tetra ... [+]
The unexpected lability of Z protecting group under mild basic conditions at room temperature is explained by a mechanism based on anchimeric assistance. It is found that the vicinal amide group stabilizes the tetrahedral intermediate formed after the nucleophilic addition of hydroxide to the carbonyl of the Z group. This effect operates in N-protected tripeptides and tetrapeptides but Z-protected dipeptides are stable under the same conditions due to the blockage of the vicinal amide NH by intramolecular H-bonding with terminal carboxylate moiety. [-]
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European Journal of Organic Chemistry, 2014(16)Rights
This is the pre-peer reviewed version of the following article:TENA‐SOLSONA, Marta, et al. Mechanistic Insight into the Lability of the Benzyloxycarbonyl (Z) Group in N‐Protected Peptides under Mild Basic Conditions. European Journal of Organic Chemistry, 2014, vol. 2014, no 16, p. 3372-3378, which has been published in final form at [http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201400154/abstract]
http://rightsstatements.org/vocab/InC/1.0/
info:eu-repo/semantics/openAccess
http://rightsstatements.org/vocab/InC/1.0/
info:eu-repo/semantics/openAccess
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