Sequential oligopeptides. Synthesis and characterization of the oligopeptides and a polypeptide with the repeating sequence L‐norvalyl‐glycyl‐L‐proline

The synthesis and characterization of a series of oligopeptides (from the tripeptide to the octadecapeptide) with the repeating sequence L‐norvalyl‐glycyl‐L‐proline and a polytripeptide with this sequence are reported. The oligomers were synthesized step by step using the mixed anhydride method. All the products were chemically and optically pure. The polymer was prepared by the active ester method, using the p‐nitrophenyl ester as the polymerizable tripeptide derivative. Good yield of relatively high average molecular‐weight polymer was obtained. In the accompanying paper conformational investigations, both in solution and in the solid state, on the oligomers and the polymer are described.

[1]  C. Toniolo,et al.  Sequential oligopeptides. Conformational studies of the oligopeptides and a polypeptide with the repeating sequence L‐norvalyl‐glycyl‐L‐proline , 1974, Biopolymers.

[2]  C. Toniolo.  CONFORMATIONAL EQUILIBRIA AND STABILITY OF OLIGOPEPTIDES , 1973 .

[3]  F. Naider,et al.  Synthesis of alanine oligopeptides with solubility-enhancing blocking groups , 1971 .

[4]  F. Naider,et al.  Conformations of alanine oligopeptides in solution , 1971 .

[5]  C. Toniolo,et al.  Circular dichroism studies of isoleucine oligopeptides in solution , 1971, Biopolymers.

[6]  C. Toniolo.  Synthesis and optical studies of isoleucine oligopeptides in solution , 1971, Biopolymers.

[7]  E. Blout,et al.  Synthesis of polypeptides and oligopeptides with the repeating sequence L-alanyl-L-prolylglycine. , 1971, Biochemistry.

[8]  M. Goodman,et al.  Conformational aspects of polypeptide structure. XXXIII. Infrared spectra and molecular conformations of γ‐ethyl L‐glutamate oligopeptides , 1971, Biopolymers.

[9]  V. Sasisekharan,et al.  Studies on the conformation of amino acids X. Conformations of norvalyl, leucyl and aromatic side groups in a dipeptide unit , 1971, Biopolymers.

[10]  G. W. Anderson,et al.  A reinvestigation of the mixed carbonic anhydride method of peptide synthesis. , 1967, Journal of the American Chemical Society.

[11]  D. Nitecki,et al.  Immunochemical studies on the poly-gamma-D-glutamyl capsule of Bacillus anthracis. II. The synthesis of eight dipeptides and four tripeptides of glutamic acid. , 1966, Biochemistry.

[12]  M. Goodman,et al.  Conformational aspects of polypeptide structure XVI. Rotatory constants, cotton effects, and ultraviolet absorption data for glutamate oligomers and co‐oligomers , 1964 .

[13]  W. S. Brinigar,et al.  Synthesis of Peptide Polymers with Repeating Sequences , 1963 .

[14]  M. Goodman,et al.  Conformational aspects of polypeptides. VIII. Helical assignments via far ultraviolet absorption spectra and optical activity , 1963 .

[15]  S. Guttmann.  Synthèse de la Val5-D-Phe8-angiotensine-I et nouvelle synthèse de la Val5-angiotensine-I , 1961 .

[16]  M. Goodman,et al.  Peptide Syntheses Via Amino Acid Active Esters1 , 1959 .

[17]  L. A. Carpino,et al.  O-Acylhydroxylamines. I. Synthesis of O-Benzoylhydroxylamine1 , 1959 .

[18]  E. Wünsch,et al.  Beiträge zur Peptidsynthese, III. Zur Darstellung von Carbobenzoxy-aminosäuren , 1958 .

[19]  G. W. Anderson,et al.  t-Butyloxycarbonylamino Acids and Their Use in Peptide Synthesis , 1957 .

[20]  M. L. Bender,et al.  The Kinetics and Oxygen Exchange of the Cupric Ion-catalyzed Hydrolysis of α-Amino Esters1 , 1957 .

[21]  E. Cherbuliez,et al.  Une nouvelle synthèse de l'oxytocine , 1955 .

[22]  A. Berger,et al.  Poly-L-proline , 1954 .

[23]  A. Berger,et al.  Cleavage of N-Carbobenzoxy Groups by dry Hydrogen Bromide and Hydrogen Chloride , 1952 .