Preparation and reactivity of aminoacyl pyroglutamates. Facile synthesis of 10-membered-ring cyclic dipeptides derived from 1,4-diaminobutyric and glutamic acids

Journal of Peptide Science

Volumn 11, Issue 3, 2005, Pages 175-186

  Chulin, A N ^a   Rodionov, I L ^a,b   Baidakova, L K ^a   Rodionova, L N ^a   Balashova, T A ^a   Ivanov, V T ^a,b  

^a SHEMYAKIN OVCHINNIKOV INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

^b INSTITUTE OF BASIC BIOLOGICAL PROBLEMS   (Russian Federation)

Author keywords

Aminoacyl incorporation reaction; Dilactams; Hoffman rearrangement; PIFA; Pyroglutamic acid; Ring expansion; Ruthenium tetroxide

Indexed keywords

AMINO ACID; BUTYRIC ACID DERIVATIVE; DIPEPTIDE; GLUTAMIC ACID DERIVATIVE; PROLINE; PYROGLUTAMIC ACID;

ARTICLE; CHEMICAL REACTION; EPIMERIZATION; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

AMINOACYLATION; AMINOBUTYRIC ACIDS; GLUTAMIC ACID; MOLECULAR STRUCTURE; ORNITHINE; OXIDATION-REDUCTION; PEPTIDES, CYCLIC; PYRROLIDONECARBOXYLIC ACID;

EID: 14844315963     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/psc.611     Document Type: Article

References (37)

1. Toniolo C. Conformationally restricted peptides through short-range cyclizations. Int. J. Pept. Protein Res. 1990; 35 287-300.
2. Manesis N, Hassan M, Glaser R, Goodman M. Bridged peptides. Synthesis, spectroscopy, and computer simulations. Biopolymers 1986; 25 S: 97-107.
3. Manesis N, Goodman M. Synthesis of a novel class of peptides: Dilactam-bridged tetrapeptides. J. Org. Chem. 1987; 52: 5331-5341.
4. Kumar A, Singh M, Chauhan VS. Synthesis of cairomycin-B, a novel bicyclic peptide containing lysine and aspartic acid. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1986; 25: 230-232.
5. Heavner GA, Audhya T, Doyle D, Tioeng FS, Goldstein G. Biologically active conformations thymopentin. Studies with conformationally restricted analogs. Int. J. Pept. Protein Res. 1991; 37: 198-209.
6. Story SC, Aldrich JV. Side-product formation during cyclization with HBTU on a solid support. Int. J. Peptide Protein Res. 1994; 43: 292-296.
7. Shemyakin MM, Antonov VK, Shkrob AM, Shchelokov VI, Agadzhanyan ZE. Activation of the amide group by acylation. Hydroxy- and aminoacyl incorporation in peptide systems. Tetrahedron 1965; 21 3537-3572.
8. Shkrob AM. Reaction of hydroxy- and amino acid incorporation. Bioorg. Khim. 1994; 20: 100-113 (Rus).
9. Antonov VK, Agadzhanyan TsE, Telesnina TR, Shemyakin MM. Aminoacyl incorporation into linear and cyclic peptides. Tetrahedron Lett. 1964; 13: 727-732.
10. Shemyakin MM, Antonov VK. Intramolecular rearrangements in peptide systems: Hydroxy- and amino-acyl incorporation into peptides. Pure Appl. Chem. 1964; 9: 75-94.
11. Glover G, Rapoport H. Amide-amide interaction via a Cyclol. J. Am. Chem. Soc. 1964; 86: 3397-3398.
12. Glover GI, Smith RB, Rapoport H. Amide-amide reaction via cyclols. J. Am. Chem. Soc. 1965; 87: 2003-2011.
13. Rothe M, Schindl W, Pudill R, Toth T, Jacob D. Reaktionen von N-(alpha-Aminoacyl)-Lactame. Tetrahedron Lett. 1969; 59: 5127-5130.
14. Kemp DS, Stites WE. A convenient preparation of derivatives of 3(S)-amino-10 (R)-carboxy-1,6-diaza-cyclodeca-2,7-dione. The dilactam of L-α,γ-diaminobutyric acid and D-glutamic acid: a β-turn template. Tetrahedron Lett. 1988; 29: 5057-5060.
15. Johnson AL, Price WA, Wong PC, Vavala RF, Stump JM. Synthesis and pharmacology of the potent angiotensin-converting enzyme inhibitor N-[1(S)-(ethoxycarbonyl)-3-phenylpropyll-(S)-alanyl-(S)-pyroglutamic acid. J. Med. Chem. 1985; 28: 1596-1602.
16. Khan SA, Erickson BW. Synthesis and regioselective hydrolysis of peptides containing an internal residue of pyroglutamic acid. J. Am. Chem. Soc. 1984; 106: 798-799.
17. 2-macroglobulin and complement proteins C3 and C4. J. Biol. Chem. 1982; 257: 11864-11867.
18. Torigoe K, Motoki Y, Muramatsu I. Ammonolysis of N-acylpyroglutamic acid. Permanganate-oxidation of peptides. II. Bull. Chem. Soc. Jpn 1981; 54: 1263-1264.
19. Yoshifuji S, Tanaka K, Kawai T, Nitta Y. A novel synthesis of L-pyroglutamic acid derivatives from L-proline. Utility of N-protecting groups for ruthenium tetroxide oxidation of cyclic alphamino acids. Chem. Pharm. Bull. 1986; 34: 3873-3878.
20. Yoshifuji S, Matsumoto H, Tanaka K, Nitta Y. The first chemical conversion of L-proline to L-glutamic acid. Tetrahedron Lett. 1980; 21: 2963-2964.
21. Bodanszky M, Martinez J. Side reaction in peptide synthesis. In The Peptides: Analysis, Synthesis, Biology, vol. 5, Gross E, Meienhofer J (eds). Academic Press: New York 1983; 112-216.
22. ca -di-tertbutyloxycarbonyl-omega-carbamoyl-alpha-amino acids and direct synthesis of protected homoglutamic acid derivatives. Chem. Pharm. Bull. 1986; 34: 3506-3509.
23. Green M, Berman J. Preparation of pentafluorophenyl esters of Fmoc protected amino acids with pentafluorophenyl trifluoroacetate. Tetrahedron Lett. 1990; 31: 5851-5852.
24. Keller O, Keller WE, van Look G, Wersin G. Tert-butoxycarbonylation of amino acids and their derivatives: N-tert-butoxycarbonylphenylalanine. Org. Synthesis 1985; 63: 160-169.
25. Loudon GM, Radhakrishna AS, Almond MR, Blodgett JK, Boutin RH. Conversion of aliphatic amides into amines with [I,I-bis(trifluoroacetoxy)iodo]benzene. 1. Scope of the reaction. J. Org. Chem. 1984; 49: 4272-4276.
26. Boutin RH, Loudon GM. Conversion of aliphatic amides into amines with [I,I-bis(trifluoroacetoxy)iodo]benzene. 2. Kinetics and mechanism. J. Org. Chem. 1984; 49: 4277-4284.
27. Chulin AN, Rodionov IL, Ivanov VT. Synthesis of 9-membered dilactams derived from 1,3-diaminopropionic and glutamic acids. J. Peptide Res. 2004; 63: 235-240.
28. Conti F, Lucente G, Romeo A, Zanotti G. Cyclols-formation from tripeptide systems and structure assignment by carbon- 13 nuclear magnetic resonance. Int. J. Pept. Protein Res. 1973; 5: 353-357.
29. Lucente G, Romeo A. Synthesis of cyclols from small peptide via amide-amide reaction. J. Chem. Soc. D. 1971; 24: 1605-1607.
30. Boyle WJ, Sifiniades S, Van Peppen JF. Asymmetric transformation of alpha-amino-epsilon-caprolactam, a lysine precursor. J. Org. Chem. 1979; 44: 4841-4847.
31. Kazmierczak P, Skulski L. A simple, two-step conversation of various iodarenes to (diacetoxyiodo)arens with chromium (VI) oxide as the oxidant. Synthesis 1998; 1721-1723.
32. Pozdnev VF. Activation of carboxylic acids by pyrocarbonates. Dialkyl pyrocarbonates as condensing reagents in the synthesis of amides of protected amino acids and peptides. Bioorg. Khim. 1996; 22 280-286 (Rus).
33. Nozaki S, Muramatsu I. Convenient synthesis of N protected amino acid amides. Bull. Chem. Soc. Jpn 1988; 61 2647-2648.
34. Lefrancier P, Bricas E. Synthese de la subunite peptidique du peptidoglycane de la paroi de trois batacteries gram-positif et de peptides de structure analogue. Bull. Soc. Chim. Biol. 1967; 49 1257-1271.
35. Anantharamaiah GM, Sivanandaiah KM. Transfer hydrogenation; method for removal of some commonly used protecting groups in peptide synthesis. J. Chem. Soc., Perkin Trans. I 1977; 5: 490-491.
36. IV ions and other oxidants. J. Chem. Soc., Faraday Trans. I 1987; 83: 2317-2329.
37. Rigo B, Lespagnol Ch, Pauly M. Studies on pyrrolidones. Synthesis of N-acylpyroglutamic esters with bactericide and fungicide properties. J. of Heterocyclic Chem. 1988; 25: 49-57.