The reaction of secondary α-amino acids with carbonyl compounds. Properties of the intermediate azomethine ylides. Oxazolidine formation versus 1.4-prototropy.

1987 ◽  
Vol 28 (48) ◽  
pp. 6077-6080 ◽  
Author(s):  
Moustafa F. Aly ◽  
Harriet Ardill ◽  
Ronald Grigg ◽  
Stephanie Leong-Ling ◽  
Shuleewan Rajviroongit ◽  
...  
Keyword(s):  
Amino Acids ◽  
Carbonyl Compounds ◽  
Azomethine Ylides

Sodium borohydride: A versatile reagent in the reductive N-monoalkylation of α-amino acids and α-amino methyl esters

2002 ◽  
Vol 80 (7) ◽  
pp. 779-788 ◽  
Author(s):  
Giancarlo Verardo ◽  
Paola Geatti ◽  
Elena Pol ◽  
Angelo G Giumanini
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Sodium Borohydride ◽  
Carbonyl Compounds ◽  
Condensation Reaction ◽  
Methyl Esters ◽  
Reducing Agent ◽  
Reductive Condensation ◽  
Versatile Reagent

α-Amino acids and α-amino methyl esters are easily converted to their N-monoalkyl derivatives by a reductive condensation reaction using several carbonyl compounds in the presence of sodium borohydride. This reducing agent has shown a wide versatility with minor but essential procedural variations. The reaction allows the α-monodeuterium labeling of the new N-substituent by use of sodium borodeuteride.Key words: α-amino acid, α-amino methyl esters, sodium borohydride, reductive N-monoalkylation, carbonyl compounds.

MCR 6: Chiral 2,6-Piperazinediones via Ugi Reactions with a-Amino Acids, Carbonyl Compounds, Isocyanides and Alcohols

Heterocycles ◽  
1998 ◽  
Vol 47 (2) ◽  
pp. 965 ◽  
Author(s):  
Ivar Ugi ◽  
Werner Hörl ◽  
Cordelia Hanusch-Kompa ◽  
Thomas Schmid ◽  
Eberhardt Herdtweck
Keyword(s):  
Amino Acids ◽  
Carbonyl Compounds

ChemInform Abstract: Azomethine Ylides from the Reaction of 4-(Dicyanomethylene)-3-methyl-1- phenyl-2-pyrazoline-5-one with α-Amino Acids and Their Esters.

ChemInform ◽  
2010 ◽  
Vol 22 (32) ◽  
pp. no-no
Author(s):  
S. A. M. METWALLY ◽  
M. F. ALY ◽  
M. A. ABD-ALLA ◽  
F. M. ATTA ◽  
M. E. ABD-EL-MONEM
Keyword(s):  
Amino Acids ◽  
Azomethine Ylides

scholarly journals How formaldehyde reacts with amino acids

2019 ◽  
Vol 2 (1) ◽  
Author(s):  
Jos J. A. G. Kamps ◽  
Richard J. Hopkinson ◽  
Christopher J. Schofield ◽  
Timothy D. W. Claridge
Keyword(s):  
Amino Acids ◽  
Carbonyl Compounds ◽  
Lysine Methylation ◽  
Low Levels

Abstract Formaldehyde is a biological electrophile produced via processes including enzymatic demethylation. Despite its apparent simplicity, the reactions of formaldehyde with even basic biological components are incompletely defined. Here we report NMR-based studies on the reactions of formaldehyde with common proteinogenic and other nucleophilic amino acids. The results reveal formaldehyde reacts at different rates, forming hydroxymethylated, cyclised, cross-linked, or disproportionated products of varying stabilities. Of the tested common amino acids, cysteine reacts most efficiently, forming a stable thiazolidine. The reaction with lysine is less efficient; low levels of an Nε-methylated product are observed, raising the possibility of non-enzymatic lysine methylation by formaldehyde. Reactions with formaldehyde are faster than reactions with other tested biological carbonyl compounds, and the adducts are also more stable. The results reveal reactions of formaldehyde with amino acids, and by extension peptides and proteins, have potential roles in healthy and diseased biology, as well as in evolution.

Sign in / Sign up

Export Citation Format

Share Document