Total Synthesis of Allene-Containing Cyclic Tetrapeptide Pseudoxylallemycin C

Synlett ◽  
2020 ◽  
Author(s):  
Alan J. Cameron ◽  
Margaret A. Brimble ◽  
Casey Park ◽  
Georgina K. Howard ◽  
Paul W. R. Harris
Keyword(s):  
Total Synthesis ◽  
Solution Phase ◽  
Linear Peptide ◽  
Rp Hplc ◽  
Cyclic Tetrapeptide

AbstractThe first total synthesis of the allene-containing cyclic tetrapeptide pseudoxylallemycin C is reported. The Tyr(t-Bu)-protected linear peptide was prepared on-resin and cyclized in solution phase to yield the protected cyclic precursor. Upon deprotection of Tyr(t-Bu), the desired phenolic cyclic tetrapeptide was separated by RP-HPLC from its epimer that also formed during the macrocyclisation step. Subsequent alkylation with 4-bromobuta-1,2-diene yielded pseudoxylallemycin C.

Investigations of the key macrolactamisation step in the synthesis of cyclic tetrapeptide pseudoxylallemycin A

2019 ◽  
Vol 17 (16) ◽  
pp. 3902-3913
Author(s):  
Alan J. Cameron ◽  
Christopher J. Squire ◽  
Ashley Gérenton ◽  
Louise A. Stubbing ◽  
Paul W. R. Harris ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Coupling Reagent ◽  
By Products ◽  
Unstable Intermediate ◽  
Cyclic Tetrapeptide

During total synthesis of pseudoxylallemycin A, an unstable intermediate was observed and appeared to be reactivated by coupling reagent by-products.

Synthesis of Dichotomin A: Use of a Penicillamine-Derived Pseudoproline to Furnish Native Valine Residues

2015 ◽  
Vol 68 (4) ◽  
pp. 627 ◽  
Author(s):  
Michelle S. Y. Wong ◽  
Deni Taleski ◽  
Katrina A. Jolliffe
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Side Chain ◽  
Linear Peptide ◽  
Cyclic Hexapeptide ◽  
Peptide Precursors ◽  
Head To Tail Cyclization

The total synthesis of cyclic hexapeptide dichotomin A from linear peptide precursors containing penicillamine-derived pseudoproline residues is reported. The incorporation of a pseudoproline residue led to a faster reaction and higher head-to-tail cyclization yields in comparison to linear precursors containing the native valine residue. However, deprotection of the pseudoproline resulted in significant amounts of a by-product in which a threonine side chain had undergone dehydration, resulting in a low overall yield of the natural product.

scholarly journals Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block

2017 ◽  
Vol 13 ◽  
pp. 919-924 ◽  
Author(s):  
Yuta Isoda ◽  
Norihiko Sasaki ◽  
Kei Kitamura ◽  
Shuji Takahashi ◽  
Sujit Manmode ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Building Block ◽  
Building Blocks ◽  
Solution Phase ◽  
Protecting Groups ◽  
Phase Synthesis ◽  
Solution Phase Synthesis

The total synthesis of TMG-chitotriomycin using an automated electrochemical synthesizer for the assembly of carbohydrate building blocks is demonstrated. We have successfully prepared a precursor of TMG-chitotriomycin, which is a structurally-pure tetrasaccharide with typical protecting groups, through the methodology of automated electrochemical solution-phase synthesis developed by us. The synthesis of structurally well-defined TMG-chitotriomycin has been accomplished in 10-steps from a disaccharide building block.

scholarly journals First total synthesis of versicotide A, B and C

RSC Advances ◽  
2020 ◽  
Vol 10 (71) ◽  
pp. 43653-43659
Author(s):  
Laura Posada ◽  
Danilo Davyt ◽  
Gloria Serra
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Anthranilic Acid ◽  
Solution Phase ◽  
Fmoc Spps

Versicotides A–C, natural products containig anthranilic acid and NMe-Ala, were prepared by Fmoc/SPPS and solution phase macrocyclization.

Solution-phase total synthesis of the hydrophilic natural product argifin using 3,4,5-tris(octadecyloxy)benzyl tag

Tetrahedron ◽  
2011 ◽  
Vol 67 (35) ◽  
pp. 6633-6643 ◽  
Author(s):  
Tomoyasu Hirose ◽  
Takako Kasai ◽  
Takafumi Akimoto ◽  
Ayako Endo ◽  
Akihiro Sugawara ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Solution Phase

Studies Toward the Total Synthesis and Stereochemical Assignment of Microspinosamide

2015 ◽  
Vol 68 (12) ◽  
pp. 1885 ◽  
Author(s):  
Gajan Santhakumar ◽  
Richard J. Payne
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Chemical Ligation ◽  
Stereochemical Assignment ◽  
Linear Peptide ◽  
Cyclic Depsipeptide ◽  
Peptide Thioester ◽  
Structural Differences

Efforts toward the total synthesis and stereochemical assignment of the cyclic depsipeptide natural product microspinosamide are described. A single diastereoisomer was targeted corresponding to the predicted structure of the natural product incorporating a (2S, 3R)-β-hydroxy-p-bromophenylalanine residue. Assembly was achieved through the initial synthesis of a cyclic depsipeptide and a linear peptide thioester fragment by solid-phase peptide synthesis, followed by fusion of the two fragments through a native chemical ligation–oxidation protocol. Extensive spectroscopic analysis showed structural differences to the isolated natural product, suggesting that a diastereoisomer of microspinosamide had been synthesised. This work lays the foundation for the future synthesis of the correct diastereoisomer.

Total Synthesis of the Fumiquinazoline Alkaloids:  Solution-Phase Studies1

2000 ◽  
Vol 65 (4) ◽  
pp. 1022-1030 ◽  
Author(s):  
Haishan Wang ◽  
A. Ganesan
Keyword(s):  
Total Synthesis ◽  
Solution Phase

Total Synthesis of the Cyclic Tetrapeptide, HC-Toxin

1983 ◽  
Vol 24 (48) ◽  
pp. 5309-5312 ◽  
Author(s):  
Megumi Kawai ◽  
Daniel H. Rich
Keyword(s):  
Total Synthesis ◽  
Hc Toxin ◽  
Cyclic Tetrapeptide
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