Document Detail

Diaminomethane dihydrochloride, a novel reagent for the synthesis of primary amides of amino acids and peptides from active esters.
MedLine Citation:
PMID:  8370644     Owner:  NLM     Status:  MEDLINE    
Amide formation from acids, N-protected amino acids and peptides was achieved in an easy and convenient way by treating "active esters" such as succinimidyl or 4-nitrophenyl esters or acyl chlorides with diaminomethane dihydrochloride in dioxane in the presence of Et3N. Diaminomethane dihydrochloride behaves as a slow ammonia-releasing agent. The method is a good alternative to the use of concentrated aqueous ammonia; it avoids solubility problems and allows better control of the stoichiometry of the reaction and of the pH. It gives good yields and does not induce racemization. The mechanism of the reaction is discussed.
G Galaverna; R Corradini; A Dossena; R Marchelli
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  International journal of peptide and protein research     Volume:  42     ISSN:  0367-8377     ISO Abbreviation:  Int. J. Pept. Protein Res.     Publication Date:  1993 Jul 
Date Detail:
Created Date:  1993-10-14     Completed Date:  1993-10-14     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0330420     Medline TA:  Int J Pept Protein Res     Country:  DENMARK    
Other Details:
Languages:  eng     Pagination:  53-7     Citation Subset:  IM    
Institute of Organic Chemistry, University of Parma, Italy.
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MeSH Terms
Amides / chemical synthesis,  chemistry
Amino Acids / chemical synthesis*,  chemistry
Ammonia / chemistry
Dipeptides / chemical synthesis*,  chemistry
Esters / chemistry
Indicators and Reagents
Reg. No./Substance:
0/Amides; 0/Amino Acids; 0/Diamines; 0/Dipeptides; 0/Esters; 0/Indicators and Reagents; 2372-88-5/diaminomethane; 7664-41-7/Ammonia

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