Development of a traceable linker containing a thiol-responsive amino acid for the enrichment and selective labelling of target proteins

Yamamoto, Jiro; Denda, Masaya; Maeda, Naomi; Kita, Miku; Komiya, Chiaki; Tanaka, Tomohiro; Nomura, Wataru; Tamamura, Hirokazu; Sato, Youichi; Yamauchi, Aiko; Shigenaga, Akira; Otaka, Akira

doi:10.1039/c4ob00622d

Cited by 11 publications

(13 citation statements)

References 35 publications

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“…3. Not only UV 13,14) butalsonear-IR(NIR)two-photonexcitation, 15) intracellular hypoxic environment, 16) thiol, 17,18) hydrogen peroxide, 19) fluoride anion, 20) and alkaline phosphatase 14) Akira Shigenaga can trigger peptide bond cleavage of Spr. Several Spr-containing peptides were already used to control function of peptides/ proteins in living cells.…”

Section: Stimulus-responsive Amino Acidmentioning

confidence: 99%

“…14,16,21) Spr has been recently employed by some other groups for in-cell imaging of a protein of interest, 21) UV-induced propulsion of a giant liposome, 22) UV-triggered nanofiber formation, 23) and tumor-targeting therapy. 24) Application of Spr in topics not mentioned in this paper 14,17,18,25,26) are detailed in our recent review. 2)…”

Section: Stimulus-responsive Amino Acidmentioning

confidence: 99%

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Development of Chemical Biology Tools Focusing on Peptide/Amide Bond Cleavage Reaction

Shigenaga

2019

CHEMICAL & PHARMACEUTICAL BULLETIN

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Peptides and proteins are involved in almost all biological events. In this review, three chemical biology tools, which were developed for peptide/protein sciences from a viewpoint of peptide/amide bond cleavage, are overviewed. First, study on an artificial amino acid that enables stimulus-responsive functional control of peptides/proteins is briefly described. Two N-S acyl transfer reaction-based tools, one a linker molecule for facile identification of target proteins of bioactive compounds and the other a reagent for selective labeling of proteins of interest, are then discussed.

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Section: Stimulus-responsive Amino Acidmentioning

confidence: 99%

Section: Stimulus-responsive Amino Acidmentioning

confidence: 99%

Development of Chemical Biology Tools Focusing on Peptide/Amide Bond Cleavage Reaction

Shigenaga

2019

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…In this study, alkyne-containing peptide 11 7 was employed as a model of the alkynylated target protein because of ease of handling and characterization of products (Figure 3). tert-Butanol was used as a cosolvent to dissolve the traceable linker.…”

Section: Click Chemistry Fluoride-induced Cleavage and Selective Lamentioning

confidence: 99%

“…We previously developed a traceable linker as an advanced cleavable linker that enables selective labeling of the target protein after elution from the streptavidin beads via the linker cleavage ( Figure 1a). 7,8 A key component of the traceable linker is a stimulus-responsive amino acid that possesses a stimulusremovable protective group (PG) on the phenolic hydroxyl group (Figure 1b). 9 The stimulus-responsive amino acid induces amide bond cleavage after stimulus-induced removal of the PG and subsequent lactonization of a trimethyl lock moiety.…”

Section: Introductionmentioning

confidence: 99%

Development of a fluoride-responsive amide bond cleavage device that is potentially applicable to a traceable linker

et al. 2014

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A fluoride-responsive (FR) amino acid that induces amide bond cleavage upon the addition of a fluoride was developed, and it was applied to a FR traceable linker. By the use of an alkyne-containing peptide as a model of an alkynylatd target protein of a bioactive compound, introduction of the FR traceable linker onto the peptide was achieved. Subsequent fluoride induced cleavage of the linker followed by labeling of the released peptide derivative was also conducted to examine the potential applicability of the FR traceable linker to the enrichment and labeling of alkynylated target molecules.

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“…5,6) Additionally, increasing utilities of unnatural amino acids as a key structural element have also been shown in fields of chemical biology and asymmetric transformation. [7][8][9][10][11] These contexts evoke much interest of synthetic chemists in asymmetric synthesis of the structural unit. 12,13) Enabling easy access to diverse α-amino acids only by changing nucleophiles employed, Mannich-type reaction of α-imino ester has been widely utilized for the asymmetric synthesis.…”

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confidence: 99%

A Convenient Method for Preparation of α-Imino Carboxylic Acid Derivatives and Application to the Asymmetric Synthesis of Unnatural α-Amino Acid Derivative

Inokuma

Jichu

Nishida

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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We describe herein a manganese(IV) oxide-mediated oxidation of N-p-methoxyphenyl (PMP)-protected glycine derivatives for the synthesis of α-imino carboxylic acid derivatives. Using this methodology, utilization of unstable glyoxic acid derivatives was avoided. Furthermore, using this methodology we synthesized novel α-imino carboxylic acid derivatives such as α-imino phenyl ester, perfluoroalkyl etsers, imides, and thioester. The asymmetric Mannich reaction of those novel imine derivatives with 1,3-dicarbonyl compound is also described, and the novel α-imino imide gave improved chemical yield and stereoselectivity compared with those obtained by the use of the conventional α-imino ester-type substrate.Key words α-imino carboxylic acid derivative; heterogeneous oxidant; asymmetric organocatalysis; thiourea; unnatural α-amino acid Unnatural α-amino acids are often seen in varieties of biologically active compounds, 1-4) including pharmaceutics, and have been used as indispensable chiral building blocks for the synthesis of such active compounds.5,6) Additionally, increasing utilities of unnatural amino acids as a key structural element have also been shown in fields of chemical biology and asymmetric transformation.7-11) These contexts evoke much interest of synthetic chemists in asymmetric synthesis of the structural unit.12,13) Enabling easy access to diverse α-amino acids only by changing nucleophiles employed, Mannich-type reaction of α-imino ester has been widely utilized for the asymmetric synthesis.14-20) Generally, condensation of glyoxalates and primary amines affords α-imino esters as the requisite substrate for Mannich-type reaction (Chart 1a); however, the glyoxalates are unstable, and suffer easy hydrolysis or polymerization at room temperature. Additionally, high susceptibility of the resulting α-imino ester to silica gel has forced us to directly use the imino esters for the Mannich reaction without purification, thereby leading to difficulty in maintaining the reaction outcome. In this context, cross-dehydrogenative coupling (CDC) has been investigated for the synthesis of α-functionalized amino acids 21-23) (Chart 1b). The CDC protocol features oxidative preparation of α-imino ester from glycinates with the use of the oxidants such as 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ), CuOAc, Ru(bpy) 3 Cl 2 / light (or N-oxyl radical), or Cu(I)/molecular oxygen, followed by in situ Mannich reaction. Although the CDC protocol is free from the use of unstable glyoxalates, the in situ Mannich reaction has to be performed in the presence of the employed oxidant due to difficulty in achieving complete separation of the imino ester and oxidant, by which the use of the CDC remains within application to the coupling of oxidant-tolerant functional units. Here, we envisioned that the heterogeneous oxidation system enabling facile removal of insoluble oxidants by filtration allowed the imino ester to be readily obtained and subsequently subjected to Mannich reaction under oxidant-free conditions (Chart 1c).

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Development of a traceable linker containing a thiol-responsive amino acid for the enrichment and selective labelling of target proteins

Cited by 11 publications

References 35 publications

Development of Chemical Biology Tools Focusing on Peptide/Amide Bond Cleavage Reaction

Development of Chemical Biology Tools Focusing on Peptide/Amide Bond Cleavage Reaction

Development of a fluoride-responsive amide bond cleavage device that is potentially applicable to a traceable linker

A Convenient Method for Preparation of α-Imino Carboxylic Acid Derivatives and Application to the Asymmetric Synthesis of Unnatural α-Amino Acid Derivative

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