Solution-Phase Peptide Synthesis; Synthesis of 'North-Western' and 'South-Eastern' Fragments of the Antifungal Cyclodepsipeptide Petriellin A

2008 ◽  
Vol 61 (8) ◽  
pp. 615 ◽  
Author(s):  
Luigi Aurelio ◽  
Robert T. C. Brownlee ◽  
Andrew B. Hughes

The solution-phase synthesis of two highly modified peptides, a hexamer and a heptamer, that constitute the two halves of the antifungal cyclic depsipeptide, Petriellin A, is reported.

1992 ◽  
Vol 45 (11) ◽  
pp. 1857 ◽  
Author(s):  
JW Perich ◽  
RB Johns

The octapeptide H-Glu-Ser-Leu-Ser-Ser-Ser-Glu-Glu-NHMe.CF3CO2H and its five shorter peptide congeners (from tripeptide to heptapeptide ) were prepared in high yield and purity by the Boc mode of solution phase peptide synthesis followed by palladium- catalysed hydrogenolytic deprotection of the six protected peptides in 50% CF3CO2H/CH3CO2H solution. The analysis of the six peptides by 13C n.m.r. spectroscopy and C18 reversed-phase chromatography suggested that a structural arrangement commenced at the hexapeptide stage and was considered to be due to the formation of a β-turn conformation.


2014 ◽  
Vol 50 (10) ◽  
pp. 1259-1261 ◽  
Author(s):  
Jianbin Wu ◽  
Guanghui An ◽  
Siqi Lin ◽  
Jianbo Xie ◽  
Wei Zhou ◽  
...  

The solution phase synthesis of N-protected amino acids and peptides has been achieved through GAP chemistry by avoiding disadvantages of the solid-phase-peptide synthesis (SPPS) and liquid-phase-peptide synthesis. The environmentally friendly GAP synthesis can substantially reduce the use of solvents, silica gels, energy and manpower.


Author(s):  
François Morvan ◽  
Aude-Emmanuelle Navarro ◽  
Cécile Dueymes ◽  
Ilaria Adamo ◽  
Andreas Schoenberger ◽  
...  

ChemInform ◽  
2010 ◽  
Vol 33 (35) ◽  
pp. 123-123
Author(s):  
Young K. Yun ◽  
John A. Porco Jr. ◽  
Jeff Labadie

2003 ◽  
Vol 6 (2) ◽  
pp. 181-184 ◽  
Author(s):  
Changhua An ◽  
Kaibin Tang ◽  
Bin Hai ◽  
Guozhen Shen ◽  
Chunrui Wang ◽  
...  

1989 ◽  
Vol 42 (9) ◽  
pp. 1519 ◽  
Author(s):  
RM Valerio ◽  
JW Perich ◽  
EA Kitas ◽  
PF Alewood ◽  
RB Johns

The PTyr (O-phosphotyrosine) pentapeptide H-Asn-Glu-Tyr(PO3H2)-Thr-Ala-OH.HO2CCF3, which is a naturally occurring sequence from the autophosphorylated Rous sarcoma virus pp60V-SrC, was prepared in high yield by the use of Boc-Tyr(PO3Me2)-OH in the Boc mode of solution-phase peptide synthesis. The protected pentapeptide, Z-Asn-Glu(OBzl)-Tyr(PO3Me2)-Thr(Bzl)-Ala-OBzl, was deprotected by a two-stage procedure which involved initial palladium-catalysed hydrogenolysis followed by the removal of the phosphate methyl groups by the use of one of the following treatments: (A) 10% bromotrimethylsilane/acetonitrile, (B) 1 M bromotrimethylsilane/thioanisole in trifluoroacetic acid, or (C) trifluoromethanesulfonic acid/trifluoroacetic acid/dimethyl sulfide/m-cresol.


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