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

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

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.

Original language	English
Pages (from-to)	2601-2604
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	20
Issue number	13
Early online date	28 Feb 2022
DOIs	https://doi.org/10.1039/D2OB00070A
Publication status	Published - 7 Apr 2022

Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/D2OB00070A

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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.",

author = "Pak-Lun Lam and Yue Wu and Ka-Leung Wong",

note = "Funding Information: 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. Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",

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doi = "10.1039/D2OB00070A",

language = "English",

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journal = "Organic and Biomolecular Chemistry",

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AU - Lam, Pak-Lun

AU - Wu, Yue

AU - Wong, Ka-Leung

N1 - Funding Information: 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. Publisher Copyright: © 2022 The Royal Society of Chemistry.

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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.

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.

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U2 - 10.1039/D2OB00070A

DO - 10.1039/D2OB00070A

M3 - Journal article

SN - 1477-0520

VL - 20

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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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