Thiol‐Ene Click Reactions – Versatile Tools for the Modification of Unsaturated Amino Acids and Peptides

Karmann, Lisa; Kazmaier, Uli

doi:10.1002/ejoc.201300672

Cited by 10 publications

(7 citation statements)

References 86 publications

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“…Another thiol-involving reaction is the thiol-ene reaction, [39] which is the addition of a thiol to an alkene through a radical intermediate, has the advantage of being promoted by UV irradiation in aqueous solvent, thus avoiding the use of a metal catalyst. [40,41] Therefore, the thiol-ene reaction has been preferred to CuAAC, despite the occurrence of side reactions, which most often involve thiol oxidation and disulfide bridge formation. This oxidation may be influenced by pH: in acidic conditions (pH ~4) the disulfide formation is effectively hindered since the thiol groups are protonated, [42] and consequently the yield of the thiol-ene reaction is improved.…”

Section: Thiol Reactionsmentioning

confidence: 99%

A Brief Guide to Preparing a Peptide–Drug Conjugate

Bugatti

2023

ChemBioChem

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Peptide–drug conjugates (PDCs) have recently emerged as interesting hybrid constructs not only for targeted therapy, but also for the early diagnosis of different pathologies. In most cases, the crucial step in the PDC synthesis is the final conjugation step, where a specific drug is bound to a particular peptide‐/peptidomimetic‐targeting unit. Thus, this concept paper aims to give a short guide to determining the finest conjugation reaction, by considering in particular the reaction conditions, the stability of the linker and the major pros and cons of each reaction. Based on the recent PDCs reported in literature, the most common and efficient conjugation methods will be systematically presented and compared, generating a short guide to consult while planning the synthesis of a novel peptide–drug conjugate.

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Section: Thiol Reactionsmentioning

confidence: 99%

A Brief Guide to Preparing a Peptide–Drug Conjugate

Bugatti

2023

ChemBioChem

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“…Karmann and Kazmier have investigated the use of TEC for the synthesis of modified amino acids, using allylglycine and a variety of thiols (Karmann and Kazmaier, 2013 ). Initial studies utilized Boc-protected allylglycine, which was reacted with a range of thiols using EtOH as a solvent under UV irradiation.…”

Section: Other Functionalizations and Applicationsmentioning

confidence: 99%

Applications of Thiol-Ene Chemistry for Peptide Science

Nolan

Scanlan

2020

Front. Chem.

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Radical thiol-ene chemistry has been demonstrated for a range of applications in peptide science, including macrocyclization, glycosylation and lipidation amongst a myriad of others. The thiol-ene reaction offers a number of advantages in this area, primarily those characteristic of “click” reactions. This provides a chemical approach to peptide modification that is compatible with aqueous conditions with high orthogonality and functional group tolerance. Additionally, the use of a chemical approach for peptide modification affords homogeneous peptides, compared to heterogeneous mixtures often obtained through biological methods. In addition to peptide modification, thiol-ene chemistry has been applied in novel approaches to biological studies through synthesis of mimetics and use in development of probes. This review will cover the range of applications of the radical-mediated thiol-ene reaction in peptide and protein science.

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“…We also reported trehalose-and eugenol-incorpolated polymer networks by thiol-ene photopolymerizations [43,44]. In the past studies, thiol-ene reactions have been applied to the modification of unsaturated amino acids [45] and to the synthesis of peptide-functionalized conjugates [46], but amino acid-based polymer network has not been prepared by use of thiolene polymerization to the best of our knowledge. In this study, triallyl L-alanine (A3A) and triallyl Lphenylalanine (A3F) whose N-and C-terminals are simultaneously modified with allyl groups were conveniently synthesized by one-pot reactions of Lalanine and L-phenylalanine with allyl bromide, respectively (Figure 1), and thermal and mechanical properties of polymer networks prepared by thiol-ene reactions of A3A and A3F with tetrathiol compounds were investigated.…”

Section: T1 Introductionmentioning

confidence: 99%

Amino acid-incorporated polymer network by thiol-ene polymerization

Yokose¹,

Shimasaki²,

Teramoto³

et al. 2015

Express Polym. Lett.

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Abstract. Triallyl L-alanine (A3A) and triallyl L-phenylalanine (A3F) were synthesized by reactions of L-alanine and L-phenylalanine with allyl bromide in the presence of sodium hydroxide, respectively. Thiol-ene thermal polymerization of A3A or A3F with pentaerythritol-based primary tetrathiol (pS4P) or pentaerythritol-based secondary tetrathiol (S4P) at allyl/SH 1/1 in the presence of 2,2"-azobis(isobutyronitrile) produced an amino acid-incorporated polymer network (A3A-pS4P, A3A-S4P or A3F-S4P). Although the thermally cured resins were homogeneous and flat films, the corresponding thiol-ene photopolymerization did not give a successful result. Degree of swelling for each thermally cured film in N,Ndimethylformamide was much higher than that in water. The glass transition and 5% weight loss temperatures (T g and T 5 ) of A3F-pS4P and A3F-S4P were higher than those of A3A-pS4P and A3A-S4P, respectively. Also, A3F-pS4P and A3F-S4P exhibited much higher tensile strengths and moduli than A3A-pS4P and A3A-S4P did, respectively. Consequently, A3F-pS4P displayed the highest T g (38.7°C), T 5 (282.0°C), tensile strength (9.5 MPa) and modulus (406 MPa) among all the thermally cured resins.

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Thiol‐Ene Click Reactions – Versatile Tools for the Modification of Unsaturated Amino Acids and Peptides

Cited by 10 publications

References 86 publications

A Brief Guide to Preparing a Peptide–Drug Conjugate

A Brief Guide to Preparing a Peptide–Drug Conjugate

Applications of Thiol-Ene Chemistry for Peptide Science

Amino acid-incorporated polymer network by thiol-ene polymerization

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