Succinimidyl Carbamate Derivatives from N‐Protected α‐Amino Acids and Dipeptides―Synthesis of Ureidopeptides and Oligourea/Peptide Hybrids

doi:10.1002/EJOC.200601010

Paper

Succinimidyl Carbamate Derivatives from N‐Protected α‐Amino Acids and Dipeptides―Synthesis of Ureidopeptides and Oligourea/Peptide Hybrids

Published May 1, 2007 · Lucile Fischer, V. Semetey, J. Lozano

European Journal of Organic Chemistry

Q2 SJR score

24

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0

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Abstract

The preparation of succinimidyl (1-{[(alkyloxy)carbonyl]amino}-1-X-methyl)carbamates (4) and succinimidyl [1-(acylamino)-1-X-methyl] carbamates (5) from a variety ofN-Boc-, -Z- or -Fmoc-protected α-amino acids and dipeptides as well as the carbamate structural characterization are described. We have previously shown that succinimidyl carbamates 5, derived from N-Boc dipeptides, can serve as direct precursors of 1,3,5-triazepan-2,6-diones, a novel class of conformationally constrained dipeptide mimetics. Herein, we have evaluated the use of these building blocks for the synthesis of ureido-peptides (in solution and on solid support), peptidyl hydantoins, oligoureas and some oligo(urea/amide) hybrids. Conformational investigations by NMR of ureidotripeptide 6i and pentamer 10, consisting of alternating amides and ureas, suggested that folded conformations (i.e. a urea turn) characterized by a cis,trans (E,Z) geometry of the urea linkage are populated in both [D5]pyridine and [D6]DMSO solutions. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

Study Snapshot

Succinimidyl carbamate derivatives from N-protected -amino acids and dipeptides can be used for the synthesis of ureidopeptides and oligourea/peptide hybrids.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Succinimidyl Carbamate Derivatives from N‐Protected α‐Amino Acids and Dipeptides―Synthesis of Ureidopeptides and Oligourea/Peptide Hybrids

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