Document Detail

Peptide synthesis in water IV. Preparation of N-ethanesulfonylethoxycarbonyl (Esc) amino acids and their application to solid phase peptide synthesis.
MedLine Citation:
PMID:  15056956     Owner:  NLM     Status:  MEDLINE    
A new N-protecting group, ethanesulfonylethoxycarbonyl (Esc), was designed to perform peptide synthesis in both aqueous and organic solvents. Esc-amino acids were prepared by the reaction of Esc-Cl and amino acids. Although Esc-Cl was a highly reactive reagent, it was not stable and decomposed during the purification procedure. A more stable reagent, ethanesulfonylethyl-4-nitrophenyl carbonate (Esc-ONp), was designed for preparation of Esc-amino acids. Esc-ONp was a stable reagent and could be purified by silica gel column chromatography or recrystallization. Esc-amino acids were prepared by the reaction of Esc-ONp and amino acids in good yield. To evaluate Esc-amino acids, Leu-enkephalin amide was synthesized using Esc-amino acids by the solid phase method in water. Removal of the Esc group was performed with 0.025 mol/l NaOH in 50% aqueous ethanol. Leu-enkephalin amide was successfully synthesized on a poly(ethylene glycol)-grafted polystyrene resin. Esc-amino acids have moderate solubility in organic solvents (such as dimethylformamide and acetonitrile). Leu-enkephalin amide was synthesized using Esc-amino acids by the solid phase method in dimethylformamide. Removal of the Esc group was performed with 0.05 mol/l tetrabutylammonium fluoride in dimethylformamide. Synthesis of Leu-enkephalin amide using Esc-amino acids in dimethylformamide was also successful. The yields of synthesis of Leu-enkephalin amide in water and dimethylformamide were 71% and 67%, respectively.
Keiko Hojo; Mitsuko Maeda; Timothy J Smith; Eriko Kita; Fumie Yamaguchi; Sachiko Yamamoto; Koichi Kawasaki
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemical & pharmaceutical bulletin     Volume:  52     ISSN:  0009-2363     ISO Abbreviation:  Chem. Pharm. Bull.     Publication Date:  2004 Apr 
Date Detail:
Created Date:  2004-04-01     Completed Date:  2004-11-10     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0377775     Medline TA:  Chem Pharm Bull (Tokyo)     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  422-7     Citation Subset:  IM    
Faculty of Pharmaceutical Sciences, Kobe Gakuin University, Japan.
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MeSH Terms
Amino Acids / chemical synthesis*,  chemistry*
Chromatography, High Pressure Liquid
Enkephalin, Leucine / chemical synthesis
Indicators and Reagents
Peptides / chemical synthesis*
Reg. No./Substance:
0/Amino Acids; 0/Indicators and Reagents; 0/Peptides; 58822-25-6/Enkephalin, Leucine; 7732-18-5/Water

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