BOP‐OXy, BOP‐OBt, and BOP‐OAt: novel organophosphinic coupling reagents useful for solution and solid‐phase peptide synthesis

El‐Faham, Ayman; Khattab, Sherine N.; Subirós‐Funosas, Ramon; Alberício, Fernando

doi:10.1002/psc.2579

Cited by 8 publications

(8 citation statements)

References 45 publications

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“…They also developed another derivative by combining Oxyma with bis (2-oxo-3-oxazolidinyl) phosphorodiamidic chloride (BOP-Cl). Through their tests, they found that the use of BOP-Oxy 43 is advantageous in most cases because of the higher coupling efficiency and more efficient suppression of racemization [57].…”

Section: Amide Bond Formationmentioning

confidence: 97%

New Methods for Chemical Protein Synthesis

Guan

Chaffey

Zeng

2014

Topics in Current Chemistry

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Chemical protein synthesis is a useful tool to generate pure proteins which are otherwise difficult to obtain in sufficient amounts for structure and property analysis. Additionally, because of the precise and flexible nature of chemical synthesis, it allows for controllable variation of protein sequences, which is valuable for understanding the relationships between protein structure and function. Despite the usefulness of chemical protein synthesis, it has not been widely adopted as a tool for protein characterization, mainly because of the lack of general and efficient methods for the preparation and coupling of peptide fragments and for the folding of polypeptide chains. To address these issues, many new methods have recently been developed in the areas of solid-phase peptide synthesis, peptide fragment assembly, and protein folding. Here we review these recent technological advances and highlight the gaps needing to be addressed in future research.

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Section: Amide Bond Formationmentioning

confidence: 97%

New Methods for Chemical Protein Synthesis

Guan

Chaffey

Zeng

2014

Topics in Current Chemistry

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“…PEGylated lactobionic acid targeted honokiol G 3 piperazine dendrimer conjugate (TPG 3 À OH)-HK-LA-PEG was prepared via carbodiimide coupling reaction. In the first step, the thirdgeneration triazine dendrimer (TPG 3 À OH) 10 was preactivated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC•HCl) in the presence of potassium salt of Oxyma as coupling reagent in acetonitrile/water mixed solvent for 5 minutes, [77][78][79][80][81][82][83][84][85] followed by addition of honokiol (HK). The reaction mixture was stirred overnight.…”

Section: Synthesis Of Peg-lactobionic Acid-honokiol-hexadeca Carboxylic Acid G 3 -Triazine Dendrimer Conjugate (Tpg 3 à Oh)-hk-la-pegmentioning

confidence: 99%

Engineered s‐Triazine‐Based Dendrimer‐Honokiol Conjugates as Targeted MMP‐2/9 Inhibitors for Halting Hepatocellular Carcinoma

et al. 2021

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Despite the advances in developing MMP-2/9 inhibitors, offtarget side effects and pharmacokinetics problems remain major challenges hindering their clinical success in cancer therapy. However, recent targeting strategies have clearly revitalized MMP research. Herein, we introduce new s-triazinebased dendrimers endowed with intrinsic MMP-2/9 inhibitory potential and tetherable to hepatocellular carcinoma-specific targeting ligands and anticancer agents via biodegradable linkages for targeted therapy. The designed dendrimeric platform was built with potential zinc-binding branching linkers (hydrazides) and termini (carboxylic acids and hydrazides) to confer potency against MMP-2/9. Preliminary cytotoxicity screening and MMP-2/9 inhibition assay of the free dendrimers revealed promising potency (MMP-9; IC 50 = 0.35-0.57 μM, MMP-2; IC 50 = 0.39-0.77 μM) within their safe doses (EC 100 = 94.15-42.75 μM). The hydrazide dendrimer was comparable to NNGH and superior to the carboxylic acid analogue. MTT assay showed that the free dendrimers were superior to the reference anticancer agent honokiol. Their anticancer potency was enhanced by HK conjugation, targeting ligands installation and PEGylation as exemplified by the hydrazide dendrimer conjugate (TPG 3 À NH 2 )-SuHK-FA-SuPEG (Huh-7; IC 50 = 5.54 μM, HepG-2; IC 50 = 10.07 μM) being 4 folds more active than HK, followed by the carboxylic acid conjugate (TPG 3 À OH)-HK-LA-PEG (Huh-7; IC 50 = 14.97, HepG-2; IC 50 = 21.29 μM). This was consistent with apoptosis studies.

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“…In 2014, our group reported novel Oxyma-based organophosphorus reagents for coupling reactions. 54 The nucleophilic additives HOBt, HOAt, OxymaPure and N-Oxyma (carboxamide instead of ethyl ester) reacted with BOP-Cl in the presence of Et 3 N, forming the corresponding phosphinic reagent (Scheme 12). Among these reagents, BOP-Oxy showed higher solubility in DMF and MeCN.…”

Section: Oxyma-based Phosphatesmentioning

confidence: 99%

OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis

et al. 2020

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OxymaPure [ethyl 2-cyano-2-(hydroxyimino)acetate] is an exceptional reagent with which to suppress racemization and enhance coupling efficiency during amide bond formation. The tremendous popularity of OxymaPure has led to the development of several Oxyma-based reagents. OxymaPure and its derived reagents are widely used in solid- and solution-phase peptide chemistry. This review summarizes the recent developments and applications of OxymaPure and Oxyma-based reagents in peptide chemistry, in particular in solution-phase chemistry. Moreover, the side reaction associated with OxymaPure is also discussed.1 Introduction2 Oxyma-Based Coupling Reagents2.1 Aminium/Uronium Salts of OxymaPure2.2 Phosphonium Salts of OxymaPure2.3 Oxyma-Based Phosphates2.4 Sulfonate Esters of OxymaPure2.5 Benzoate Esters of OxymaPure2.6 Carbonates of OxymaPure Derivatives3 OxymaPure Derivatives4 Other Oxime-Based Additives and Coupling Reagents5 Side Reactions Using OxymaPure Derivatives6 Conclusion7 List of Abbreviations

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BOP‐OXy, BOP‐OBt, and BOP‐OAt: novel organophosphinic coupling reagents useful for solution and solid‐phase peptide synthesis

Cited by 8 publications

References 45 publications

New Methods for Chemical Protein Synthesis

New Methods for Chemical Protein Synthesis

Engineered s‐Triazine‐Based Dendrimer‐Honokiol Conjugates as Targeted MMP‐2/9 Inhibitors for Halting Hepatocellular Carcinoma

OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis

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