Exploring Solution-Phase Cyclization and Sulfamyl Safety-Catch Resin Strategies for the Total Synthesis of the Marine Antimicrobial Cyclic Tetrapeptide Cyclo(GSPE)

2012 ◽  
Vol 19 (1) ◽  
pp. 25-31 ◽  
Author(s):  
Huichang A. Lim ◽  
Lik Tong Tan ◽  
C. S. Brian Chia
Keyword(s):  
Total Synthesis ◽  
Solution Phase ◽  
Cyclic Tetrapeptide

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.

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

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

scholarly journals Hybrid phase ligation for efficient synthesis of histone proteins

2016 ◽  
Vol 14 (9) ◽  
pp. 2603-2607 ◽  
Author(s):  
Ruixuan R. Yu ◽  
Santosh K. Mahto ◽  
Kurt Justus ◽  
Mallory M. Alexander ◽  
Cecil J. Howard ◽  
...  
Keyword(s):  
Solid Solution ◽  
Total Synthesis ◽  
Solid Phase ◽  
Solution Phase ◽  
Solid Solution Phase ◽  
Efficient Synthesis ◽  
Histone Proteins

We report a hybrid solid-solution phase ligation approach that combines the efficiency of solid phase ligation with solution phase ligation in the total synthesis of modified histone proteins.

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