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

Pak-Lun Lam; Yue Wu; Ka-Leung Wong

doi:10.1039/d2ob00070a

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

Pak-Lun Lam
, Yue Wu^*
, Ka-Leung Wong^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

1 Citation (Scopus)

Abstract

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. © 2022 The Royal Society of Chemistry.

Original language	English
Pages (from-to)	2601-2604
Journal	Organic and Biomolecular Chemistry
Volume	20
Issue number	13
Online published	28 Feb 2022
DOIs	https://doi.org/10.1039/d2ob00070a
Publication status	Published - 7 Apr 2022
Externally published	Yes

Funding

This work was supported by grants from the Hong Kong Research Grant Council (HKBU 12300021), the CAS-Croucher Funding Scheme for Joint Laboratories (CAS18204), the Hong Kong Research Grants Council Collaborative Research Fund Scheme (C4001-18GF), BP, Tsinghua, the HKBU Joint Lab for EBV associated Cancer and Health and Medical Research Fund (18170022) and Hong Kong Baptist University RC-ICRS/18-19/02A. KLW thanks HKBU for the Dr Mok Man Hung Endowed Professorship.

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

abstract = "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. {\textcopyright} 2022 The Royal Society of Chemistry.",

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AU - Wu, Yue

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PY - 2022/4/7

Y1 - 2022/4/7

N2 - 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. © 2022 The Royal Society of Chemistry.

AB - 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. © 2022 The Royal Society of Chemistry.

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U2 - 10.1039/d2ob00070a

DO - 10.1039/d2ob00070a

M3 - RGC 21 - Publication in refereed journal

C2 - 35258068

SN - 1477-0520

VL - 20

SP - 2601

EP - 2604

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 13

ER -

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

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

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