Solution‐Phase Peptide Synthesis

Tsuda, Yuko; Okada, Yoshio

doi:10.1002/9783527631803.ch6

Cited by 4 publications

(3 citation statements)

References 301 publications

(197 reference statements)

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“…In solution phase synthesis, two amino acids are coupled in solution, the first being protected at the carboxyl group and the second protected at the N-terminus group [36]. Before each addition of amino acids, the intermediate peptides are isolated, purified and characterized; the N-terminus protective group is removed to allow coupling with the next N-terminus protected amino acid.…”

Section: Synthetic and Recombinant Peptidesmentioning

confidence: 99%

Establishment of measurement traceability for peptide and protein quantification through rigorous purity assessment—a review

Josephs

Martos

et al. 2019

Metrologia

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The health of their populations and efficient health care systems are of critical importance to the economic and social well-being of nations. Accurate and comparable peptide/protein measurements are required in support of diagnosis, prognosis, monitoring and treatment of widespread diseases (e.g. diabetes). The required consistency of measurement results can be achieved by making them traceable to stated references and through the development of Reference Measurement Systems. The review mainly concentrates on the progress made in the Protein Analysis Working Group of the Consultative Committee for Amount of Substance: Metrology in Chemistry and Biology (CCQM-PAWG) in establishing Primary Calibration Reference Services in the emerging area of health markers such as peptides/proteins. Primary Calibration Reference Services are technical capabilities for composition assignment, commonly as the mass fraction content, of pure substances or solutions thereof. It is a core technical competency for National Measurement Institutes (NMIs). A limited number of key comparisons, foreseen by the CCQM-PAWG strategy, are discussed that enable NMIs providing measurement services in peptide/protein analysis to test and demonstrate their capabilities. In addition, the review examines the development and improvement of analytical methods and metrological models that are required to meet the needs of NMIs and associated clinical stakeholders.

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Section: Synthetic and Recombinant Peptidesmentioning

confidence: 99%

Establishment of measurement traceability for peptide and protein quantification through rigorous purity assessment—a review

Josephs

Martos

et al. 2019

Metrologia

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“…It also suffers poor green credentials: protecting groups, atom inefficiency, high E-factor and low process mass intensity, Scheme 1b, Table 2. [12][13][14] Biosynthesis methods are leading the way in synthesis of longer peptides, for example in insulin manufacture, 15 but are unproductive for short peptides. For example proteases are used to couple protected amino acids, but rely on high enzyme loadings and displacing unfavourable equilibria with either excess reagents, solubility effects or organic solvents, Scheme 1c.…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, organic solution phase synthesis (SPS), which uses similar chemical methodology to SPPS, is the main method for small peptide manufacture. It also suffers poor green credentials: protecting groups, atom inefficiency, a high E-factor, and low process mass intensity, Scheme b, Table . − Biosynthesis methods are leading the way in synthesis of longer peptides, for example in insulin manufacture, but are unproductive for short peptides. For example proteases are used to couple protected amino acids, but rely on high enzyme loadings and displacing unfavorable equilibria with either excess reagents, solubility effects, or organic solvents, Scheme c. ,− Surprisingly, the pioneering work done in the 1950–60s by Bartlett and Hirschmann describing the coupling of N -carboxyanhydride (NCA or Leuch’s anhydride) to amino acids has not been widely adopted, despite it being productive, cost-effective, and green, Scheme . − …”

Section: Introductionmentioning

confidence: 99%

Highly Productive Continuous Flow Synthesis of Di- and Tripeptides in Water

Jolley

Nye

Niño

et al. 2017

Org. Process Res. Dev.

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The reaction of amino acid derived N-carboxyanhydrides (NCAs) with unprotected amino acids under carefully controlled aqueous continuous flow conditions realized the formation of range of di-and tripeptide products in 60-85% conversion at productivities of up to 535 g.L-1 h-1. This required a fundamental understanding of the physicochemical aspects of the reaction resulting in the design of a bespoke continuous stirred tank reactor (CSTR) with continuous solids addition, high shear mixing, automated pH control to avoid the use of buffer, and efficient heat removal to control the reaction at 1±1 °C.

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Making Solid‐Phase Peptide Synthesis Greener: A Review of the Literature

Varnava

Sarojini

2019

Chemistry An Asian Journal

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To date, the synthesis of peptides is concurrent with the production of enormous amounts of toxic waste. DMF, CH2Cl2, and NMP are three of the most toxic organic solvents used in chemical synthesis and are the most common solvents used for peptide synthesis. Additionally, concerns about the hepatotoxicity caused by exposure to DMF and from the toxic and allergenic nature of additives used in peptide synthesis necessitates the need for a green, environmentally friendly, and safer protocol for peptide synthesis. This review summarizes the current literature on green solid‐phase peptide synthesis successes and challenges encountered. The review concludes with suggestions for future research towards a simple and efficient green peptide synthesis protocol.

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Solution‐Phase Peptide Synthesis

Cited by 4 publications

References 301 publications

Establishment of measurement traceability for peptide and protein quantification through rigorous purity assessment—a review

Establishment of measurement traceability for peptide and protein quantification through rigorous purity assessment—a review

Highly Productive Continuous Flow Synthesis of Di- and Tripeptides in Water

Making Solid‐Phase Peptide Synthesis Greener: A Review of the Literature

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