Nα-Amino acid containing privileged structures: design, synthesis and use in solid-phase peptide synthesis

Literature Information

Publication Date 2018-07-12
DOI 10.1039/C8OB01485J
Impact Factor 3.876
Authors

Eva Schütznerová, Adam Přibylka


View Original

Abstract

Fmoc-protected Nα-amino acid containing heterocyclic privileged structures, O-(1-methyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl)-L-serine and O-((S)-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)-L-serine, were synthesized on the solid phase from simple commercially available building blocks under mild conditions. The amino acid side-chain is composed of tetramic acid, a natural product derived privileged structure. The key transformation was the formation of cyclic enol ethers via nonclassical Wittig olefinations of the esters. Solid-phase synthesis represents a method of choice, particularly for the synthesis of peptides. This route is compatible with traditional Merrifield solid-phase peptide synthesis (SPPS), as documented on the preparation of the pentapeptide Leu-enkephalin amide H-Tyr-Gly-Gly-Phe-Leu-NH2 with Phe or Tyr replaced by a novel amino acid.

Related Literature

Electrochemical oxidation mechanisms for selective products due to C–O and C–C cleavages of β-O-4 linkages in lignin model compounds

Jing Chen, Hanling Yang, Hongquan Fu, Hongyan He, Qiang Zeng, Xuehui Li

2020-04-28 Paper

DOI: 10.1039/D0CP01091J

Strain induced spin-splitting and half-metallicity in antiferromagnetic bilayer silicene under bending

Jin-Lei Shi, Xing-Ju Zhao, Yu-Zhong Zhang, Su-Huai Wei

2020-04-24 Paper

DOI: 10.1039/D0CP01350A

Solvent similarity index

Mark D. Driver, Christopher A. Hunter

2020-05-15 Paper

DOI: 10.1039/D0CP01570A

Excited-state proton transfer in protonated adrenaline revealed by cryogenic UV photodissociation spectroscopy

Jordan Dezalay, Michel Broquier, Satchin Soorkia

2020-04-28 Paper

DOI: 10.1039/D0CP01127D

Back cover

Cover

DOI: 10.1039/D0CP90134B

Effect of zeolite morphology on charge separated states: ZSM-5-type nanocrystals, nanosheets and nanosponges

Lucie Duplouy, Alain Moissette, Matthieu Hureau, Vincent De Waele, Isabelle Batonneau-Gener

2020-05-07 Paper

DOI: 10.1039/D0CP01701A

Charge fluctuations from molecular simulations in the constant-potential ensemble

Laura Scalfi, Sara Bonella, Paul A. Madden

2019-12-13 Paper

DOI: 10.1039/C9CP06285H

Surface-orientation- and ligand-dependent quenching of the spin magnetic moment of Co porphyrins adsorbed on Cu substrates

Md. Ehesan Ali, Matthias Bernien, Nino Hatter, Fabian Nickel, Lalminthang Kipgen, Christian F. Hermanns, Timo Bißwanger, Philip Loche, Benjamin W. Heinrich, Katharina J. Franke, Peter M. Oppeneer, Wolfgang Kuch

2020-05-18 Paper

DOI: 10.1039/D0CP00854K

Inside back cover

Cover

DOI: 10.1039/D0CP90122A

You might also like

Compound Q&A

What are the main uses of 4-Nitrophenyl phosphate disodium salt hexahydrate (CAS: 333338-18-4)?

4-Nitrophenyl phosphate disodium salt hexahydrate is primarily used as a substra...

333338-18-44-Nitrophenyl phosph...
Compound Q&A

What are the main uses of 2-(Trifluoromethyl)-1,3-oxazole-4-carboxylic Acid (CAS: 1060816-01-4)?

2-(Trifluoromethyl)-1,3-oxazole-4-carboxylic Acid (CAS: 1060816-01-4) is widely ...

1060816-01-42-(Trifluoromethyl)-...
Compound Q&A

How should 2-Fluoro-4-biphenylcarboxylic acid (CAS: 137045-30-8) be stored?

2-Fluoro-4-biphenylcarboxylic acid should be stored in a cool, dry place at room...

137045-30-82-Fluoro-4-biphenylc...
Compound Q&A

What industries use Prednisolone-21-Carboxylic Acid (CAS: 61549-70-0)?

Prednisolone-21-Carboxylic Acid is primarily used in the pharmaceutical industry...

61549-70-0Prednisolone-21-Carb...
Compound Q&A

How should 4-(Hydrazinomethyl)-1,2,3-benzenetriol (CAS: 3614-72-0) be stored?

4-(Hydrazinomethyl)-1,2,3-benzenetriol (CAS: 3614-72-0) should be stored in a co...

3614-72-04-(Hydrazinomethyl)-...
Compound Q&A

What industries use 4-Amino-1-methyl-1H-pyrazole-5-carboxylic acid hydrochloride (CAS: 92534-70-8)?

4-Amino-1-methyl-1H-pyrazole-5-carboxylic acid hydrochloride (CAS: 92534-70-8) i...

92534-70-84-Amino-1-methyl-1H-...
Compound Q&A

What regulatory guidelines apply to dehydropachymic acid (CAS: 77012-31-8)?

Dehydropachymic acid (CAS: 77012-31-8) is regulated by various agencies. It fall...

77012-31-8Dehydropachymic acid
Compound Q&A

What is the market or research trend for 6-[(2,2-Dimethylpropanoyl)amino]nicotinic acid (CAS: 898561-66-5)?

The market and research trends for 6-[(2,2-Dimethylpropanoyl)amino]nicotinic aci...

898561-66-56-[(2,2-Dimethylprop...
Compound Q&A

How should 1,10-Phenanthroline-2,9-dicarbaldehyde (CAS: 57709-62-3) be stored?

1,10-Phenanthroline-2,9-dicarbaldehyde should be stored in a cool, dry place awa...

57709-62-31,10-Phenanthroline-...
Compound Q&A

How is 5-Carbamoyl-11-oxo-10,11-dihydro-5H-dibenzo[b,f]azepin-10-yl acetate (CAS: 113952-21-9) typically synthesized?

5-Carbamoyl-11-oxo-10,11-dihydro-5H-dibenzo[b,f]azepin-10-yl acetate can be synt...

113952-21-95-Carbamoyl-11-oxo-1...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.