Evaluation of greener solvents for solid-phase peptide synthesis

被引：33

作者：

Wegner, Katarzyna ^{[1
]}

Barnes, Danielle ^{[1
]}

Manzor, Kim ^{[1
]}

Jardine, Agnieszka ^{[1
]}

Moran, Declan ^{[1
]}

机构：

[1] Ipsen Mfg Ireland Ltd, APID Dept, Snugborough Rd, Dublin D15, Ireland

来源：

GREEN CHEMISTRY LETTERS AND REVIEWS | 2021年 / 14卷 / 01期

关键词：

Green chemistry; greener solvents; solvent evaluation; peptides; solid-phase peptide synthesis;

D O I：

10.1080/17518253.2021.1877363

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Polar aprotic solvents such as N,N-Dimethylformamide (DMF), N-methyl-2-pyrrolidone (NMP), N,N'-dimethylacetamide (DMAc) and chlorinated solvent such dichloromethane (DCM) are the most widely used solvents for Fmoc solid-phase peptide synthesis (SPPS). These solvents are considered hazardous chemicals but are normally used in large amounts for washing, deprotection, and coupling steps during SPPS. DMF, DMAc and NMP are classified as toxic for reproduction in accordance with Article 57(c) of REACH (Registration, Evaluation Authorization and Restriction of CHemicals) and were identified as SVHC (Substance Very High Concern). The aim of this study was to find a greener solvent alternative which could replace DMF in SPPS manufacturing processes at Ipsen. Greener solvents which demonstrated efficient resin swelling and solubility were selected as candidates for SPPS trials for the small-scale synthesis of commercial and developmental peptides.

引用

页码：152 / 163

页数：12

共 45 条

[21] Green Solvent Mixtures for Solid-Phase Peptide Synthesis: A Dimethylformamide-Free Highly Efficient Synthesis of Pharmaceutical-Grade Peptides [J].

Ferrazzano, Lucia ;

Corbisiero, Dario ;

Martelli, Giulia ;

Tolomelli, Alessandra ;

Viola, Angelo ;

Ricci, Antonio ;

Cabri, Walter .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (15) :12867-12877

[22] SOLVATION EFFECTS IN SOLID-PHASE PEPTIDE-SYNTHESIS [J].

FIELDS, GB ;

FIELDS, CG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4202-4207

[23] Expanding GSK's solvent selection guide - embedding sustainability into solvent selection starting at medicinal chemistry [J].

Henderson, Richard K. ;

Jimenez-Gonzalez, Concepcion ;

Constable, David J. C. ;

Alston, Sarah R. ;

Inglis, Graham G. A. ;

Fisher, Gail ;

Sherwood, James ;

Binks, Steve P. ;

Curzons, Alan D. .

GREEN CHEMISTRY, 2011, 13 (04) :854-862

[24] Sustainability Challenges in Peptide Synthesis and Purification: From R&D to Production [J].

Isidro-Llobet, Albert ;

Kenworthy, Martin N. ;

Mukherjee, Subha ;

Kojach, Michael E. ;

Wegner, Katarzyna ;

Gallou, Fabrice ;

Smith, Austin G. ;

Roschangar, Frank .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (08) :4615-4628

[25] Green Solid-Phase Peptide Synthesis (GSPPS) 3. Green Solvents for Fmoc Removal in Peptide Chemistry [J].

Jad, Yahya E. ;

Govender, Thavendran ;

Kruger, Hendrik G. ;

El-Faham, Ayman ;

de la Torre, Beatriz G. ;

Albericio, Fernando .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2017, 21 (03) :365-369

[26] Green Solid-Phase Peptide Synthesis 2.2-Methyltetrahydrofuran and Ethyl Acetate for Solid-Phase Peptide Synthesis under Green Conditions [J].

Jad, Yahya E. ;

Acosta, Gerardo A. ;

Govender, Thavendran ;

Kruger, Hendrik G. ;

El-Faham, Ayman ;

de la Torre, Beatriz G. ;

Albericio, Fernando .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2016, 4 (12) :6809-6814

[27] Mechanochemical Preparation of 3,5-Disubstituted Hydantoins from Dipeptides and Unsymmetrical Ureas of Amino Acid Derivatives [J].

Konnert, Laure ;

Gonnet, Lori ;

Halasz, Ivan ;

Suppo, Jean-Simon ;

de Figueiredo, Renata Marcia ;

Campagne, Jean-Marc ;

Lamaty, Frederic ;

Martinez, Jean ;

Colacino, Evelina .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (20) :9802-9809

[28] Solventless Synthesis of N-Protected Amino Acids in a Ball Mill [J].

Konnert, Laure ;

Gauliard, Anne ;

Lamaty, Frederic ;

Martinez, Jean ;

Colacino, Evelina .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (09) :1186-1191

[29] Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis [J].

Kumar, Ashish ;

Sharma, Anamika ;

de la Torre, Beatriz G. ;

Albericio, Fernando .

MOLECULES, 2019, 24 (21)

[30] Microwave-Assisted Green Solid-Phase Peptide Synthesis Using γ-Valerolactone (GVL) as Solvent [J].

Kumar, Ashish ;

Jad, Yahya E. ;

Collins, Jonathan M. ;

Albericio, Fernando ;

de la Torre, Beatriz G. .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2018, 6 (06) :8034-8039

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