Incorporation of Fmoc-Dab(Mtt)-OH during solid-phase peptide synthesis: a word of caution

As a commercially available and orthogonally protected amino acid building block, Fmoc-Dab(Mtt)-OH showed abnormally poor coupling efficiency during solid-phase peptide synthesis (SPPS). Herein, we reveal that Fmoc-Dab(Mtt)-OH undergoes rapid lactamization under a series of conditions with various c...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-03, Vol.2 (13), p.261-264
Main Authors: Lam, Pak-Lun, Wu, Yue, Wong, Ka-Leung
Format: Article
Language:English
Subjects:
Amino acids
Amino Acids - chemistry
Coupling
Fluorenes - chemistry
Indicators and Reagents
Peptide synthesis
Peptides
Peptides - chemistry
Reagents
Solid phases
Solid-Phase Synthesis Techniques - methods
Synthesis
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Summary:As a commercially available and orthogonally protected amino acid building block, Fmoc-Dab(Mtt)-OH showed abnormally poor coupling efficiency during solid-phase peptide synthesis (SPPS). Herein, we reveal that Fmoc-Dab(Mtt)-OH undergoes rapid lactamization under a series of conditions with various coupling reagents. Although the complete incorporation of Fmoc-Dab(Mtt)-OH can be achieved using a multi-time and preincubation-free protocol with the coupling reagent DEPBT, alternative orthogonally protected building blocks are suggested to be used for avoiding such a costly and tedious procedure. As a commercially available and orthogonally protected amino acid building block, Fmoc-Dab(Mtt)-OH showed abnormally poor coupling efficiency during solid-phase peptide synthesis (SPPS).
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00070a