2018年11月12日月曜日

Get Access to CPME 2018

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2018年11月2日金曜日

Green Peptide Synthesis 2018


Research Article


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Microwave-Assisted Green Solid-Phase Peptide Synthesis Using γ-Valerolactone (GVL) as Solvent

† School of Chemistry and Physics, University of KwaZulu-Natal, University Road, Westville, Durban 4001, South Africa
‡ Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, University Road, Westville, Durban 4001, South Africa
§ CEM Corporation, 3100 Smith Farm Road, Matthews, North Carolina 28104, United States
∥ Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1-11, Barcelona 08028, Spain
⊥ CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10, Barcelona 08028, Spain
# KRISP, College of Health Sciences, University of KwaZulu-Natal, Durban 4001, South Africa
ACS Sustainable Chem. Eng., 2018, 6 (6), pp 8034–8039
DOI: 10.1021/acssuschemeng.8b01531
Publication Date (Web): April 29, 2018
Copyright © 2018 American Chemical Society
Cite this:ACS Sustainable Chem. Eng. 2018,  6, 6, 8034-8039

Synopsis

A combination of nature and technology, helping to make greener the synthesis of peptides, is reported.

Abstract


Abstract Image
 
 
 
The increasing demand for synthetic peptides in various research fields raises a challenge, namely, the development of greener methods for their preparation. Here we report on an ecofriendly solid-phase peptide synthesis (SPPS) methodology. Substitution of the hazardous solvent DMF by the biomass-derived organic solvent γ-valerolactone (GVL), together with the application of microwave-assisted automated SPPS, allowed the synthesis of peptides with a wide range of lengths and high purity using polystyrene- and polyethylene-glycol-based resins. The yields achieved were comparable to those obtained with standard methodologies. To date, this is the greenest approach reported in terms of the solvent used, waste generated, and energy efficiency.

Keywords:

Automatic synthesis; Green solvent; Peptide; Sustainable chemistry
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acssuschemeng.8b01531.
  • HPLC and MS data of the synthesized peptides (PDF)

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Article Views: 204 Times
Received 4 April 2018
Published online 29 April 2018
Published in print 4 June 2018
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2018年10月31日水曜日

Ni- Coupling @ ACS 2018


Ni-Catalyzed Cross Coupling @ ACS


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Ni - & Fe- Catalyzed Coupling 2013~


Review


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Ni- and Fe-Catalyzed Cross-Coupling Reactions of Phenol Derivatives

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States
Org. Process Res. Dev., 2013, 17 (1), pp 29–39
DOI: 10.1021/op300236f
Publication Date (Web): December 11, 2012
Copyright © 2012 American Chemical Society
Cite this:Org. Process Res. Dev. 2013,  17, 1, 29-39

Abstract



Abstract Image
 
 
 
This review describes our laboratory’s efforts to develop transition metal-catalyzed cross-couplings of several unconventional phenol-based electrophiles. Specifically, we highlight herein the following four key transformations: (a) nickel-catalyzed Suzuki–Miyaura couplings of aryl pivalates, carbamates, and sulfamates to construct sp2–sp2 C–C bonds; (b) iron-catalyzed Kumada couplings of aryl carbamates and sulfamates for the assembly of sp2–sp3 C–C bonds; (c) nickel-catalyzed amination reactions of carbamates and sulfamates to build aryl C–N bonds; and (d) nickel-catalyzed reductive cleavage reactions of aryl carbamates to achieve aryl deoxygenation and a rare method for cine substitution. We expect this review will enable the greater use of unconventional phenol-based cross-coupling electrophiles in industrial settings.
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Article Views: 6,678 Times
Received 28 August 2012
Published online 11 December 2012
Published in print 18 January 2013

Review

Previous Article
Table of Contents

Ni- and Fe-Catalyzed Cross-Coupling Reactions of Phenol Derivatives

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States
Org. Process Res. Dev., 2013, 17 (1), pp 29–39
DOI: 10.1021/op300236f
Publication Date (Web): December 11, 2012
Copyright © 2012 American Chemical Society
Cite this:Org. Process Res. Dev. 2013,  17, 1, 29-39

Abstract

Abstract Image
This review describes our laboratory’s efforts to develop transition metal-catalyzed cross-couplings of several unconventional phenol-based electrophiles. Specifically, we highlight herein the following four key transformations: (a) nickel-catalyzed Suzuki–Miyaura couplings of aryl pivalates, carbamates, and sulfamates to construct sp2–sp2 C–C bonds; (b) iron-catalyzed Kumada couplings of aryl carbamates and sulfamates for the assembly of sp2–sp3 C–C bonds; (c) nickel-catalyzed amination reactions of carbamates and sulfamates to build aryl C–N bonds; and (d) nickel-catalyzed reductive cleavage reactions of aryl carbamates to achieve aryl deoxygenation and a rare method for cine substitution. We expect this review will enable the greater use of unconventional phenol-based cross-coupling electrophiles in industrial settings.
View: ACS ActiveView PDF | PDF | PDF w/ Links | Full Text HTML

Citation data is made available by participants in Crossref's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search inSciFinder.

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Add to ACS ChemWorx
Explore by:

Metrics Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.

Article Views: 6,678 Times
Received 28 August 2012
Published online 11 December 2012
Published in print 18 January 2013
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