Bergmann azlactone synthesis

The Bergmann-Azlactone-Synthesis (also known as Bergmann-Stern-Azlactone-Synthesis) is a name reaction from the field of organic chemistry . The reaction was named after the German-American chemist Max Bergmann (1886–1944) and is a classic synthesis for the production of dipeptides .

Overview reaction

The Bergmann azlactone synthesis is used to produce peptides 3 , especially dipeptides from an azlactone 1 and an amino acid 2 :

Reaction mechanism

The reaction of azlactone 1 with amino acid 2 opens the azlactone ring. An acylated unsaturated dipeptide 4 is formed , which is converted to the saturated dipeptide 5 by catalytic hydrogenation . Subsequent catalytic cleavage of acetic acid produces dipeptide 3 .

Individual evidence

^ Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , pp. 353 , doi : 10.1002 / 9780470638859 ( wiley.com ).
↑ ^a ^b Wolfgang Steglich , Rudolf Hurnaus: About the course of Bergmann-Stern's azlactone synthesis; 2-alkylidene-pseudooxazolone- (5) , Tetrahedron Lett., 1966, 383, doi: 10.1016 / S0040-4039 (00) 72951-0 .
↑ J. Plöchl: About phenylglycidic acid (phenyloxacrylic acid) , reports of the German Chemical Society , 1883, 16, 2815, doi: 10.1002 / cber.188301602235 .
^ JS Fruton, Advan. Protein Chem. V, 15 (1949); S. Archer in Amino Acids and Proteins, DM Greenberg, Ed. (Thomas, Springfield, IL, 1951) p 181; HD Springall, The Structural Chemistry of Proteins (New York, 1954) p. 29; E. Baltazzi, Quart. Rev. (London) 10, 235 (1956). Cf.

[1] Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , pp. 353 , doi : 10.1002 / 9780470638859 ( wiley.com ).

[Steglich_Hurnaus-2] Wolfgang Steglich , Rudolf Hurnaus: About the course of Bergmann-Stern's azlactone synthesis; 2-alkylidene-pseudooxazolone- (5) , Tetrahedron Lett., 1966, 383, doi: 10.1016 / S0040-4039 (00) 72951-0 .

[3] J. Plöchl: About phenylglycidic acid (phenyloxacrylic acid) , reports of the German Chemical Society , 1883, 16, 2815, doi: 10.1002 / cber.188301602235 .

[4] JS Fruton, Advan. Protein Chem. V, 15 (1949); S. Archer in Amino Acids and Proteins, DM Greenberg, Ed. (Thomas, Springfield, IL, 1951) p 181; HD Springall, The Structural Chemistry of Proteins (New York, 1954) p. 29; E. Baltazzi, Quart. Rev. (London) 10, 235 (1956). Cf.