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An efficient method for the synthesis of phenacyl ester‐protected dipeptides using neutral alumina‐supported sodium carbonate ‘Na 2 CO 3 /n‐Al 2 O 3 ’
Author(s) -
Hashimoto Chikao,
Sugimoto Kazuhiro,
Takahashi Youhei,
Kodomari Mitsuo
Publication year - 2013
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.2544
Subject(s) - dipeptide , chemistry , yield (engineering) , trifluoroacetic acid , base (topology) , amino acid , phenacyl , peptide synthesis , peptide , organic chemistry , stereochemistry , medicinal chemistry , combinatorial chemistry , biochemistry , mathematical analysis , materials science , mathematics , metallurgy
In the synthesis of dipeptides (Boc‐AA 1 ‐AA 2 ‐OPac: AA 1 and AA 2 represent amino acids) protected by phenacyl (Pac) ester, amines and solid bases as the base for the conversion of the trifluoroacetic acid (TFA) salt of the amino component (TFA·H‐AA 2 ‐OPac) into the corresponding free amino component (H‐AA 2 ‐OPac) were examined. The synthesis of a dipeptide (Boc‐Ala‐Gly‐OPac) using amines for the conversion afforded an unsatisfactory yield with by‐products. On the other hand, the use of neutral alumina‐supported Na 2 CO 3 (Na 2 CO 3 /n‐Al 2 O 3 ) as a solid base for the conversion provided the dipeptide in a quantitative yield without by‐products. The application of Na 2 CO 3 /n‐Al 2 O 3 to the synthesis of some dipeptides protected by Pac ester gave the desired peptides in excellent yields. Copyright © 2013 European Peptide Society and John Wiley & Sons, Ltd.