Stereoselective acylation of a racemic amine with Cα- methyl phenylglycine-based dipeptide 5(4H)-oxazolones

Chirality

Volumn 17, Issue 8, 2005, Pages 481-487

  Moretto, Alessandro ^a   Peggion, Cristina ^a   Formaggio, Fernando ^a   Crisma, Marco ^a   Kaptein, Bernard ^b   Broxterman, Quirinus B ^b   Toniolo, Claudio ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b DSM RESEARCH   (Netherlands)

Author keywords

turn; Amino acid; Chirality; Diastereoselectivity; HPLC; IR absorption; Peptides; X ray diffraction

Indexed keywords

ALPHA METHYLPHENYLGLYCINE; DIPEPTIDE; OXAZOLONE; PHENYLGLYCINE; UNCLASSIFIED DRUG;

ACETYLATION; ACYLATION; AMINATION; AMINOLYSIS; ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; PEPTIDE ANALYSIS; POLARIZATION; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION ANALYSIS; SENSITIVITY ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; TEMPERATURE MEASUREMENT; THREE DIMENSIONAL IMAGING; X RAY DIFFRACTION;

ACYLATION; AMINO ACIDS, CYCLIC; CRYSTALLOGRAPHY, X-RAY; DIPEPTIDES; GLYCINE; OXAZOLONE; PROTEIN CONFORMATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM; X-RAY DIFFRACTION;

EID: 25844466954     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20182     Document Type: Article

References (41)

1. Kondo K, Kurosaki T, Murakami Y. Enantioselective N-acylation of racemic secondary alkyl amines with chiral 2-acetylamino-2́-diacetylamino-1, 1′-binaphthyl. Synlett 1998;725-726.
2. Al-Sehemi AG, Atkinson RS, Fawcett J, Russell DR. 3-(N,N-Diacylamino) quinazolin-4(3H)-ones as enantioselective acylating agents for amines. Tetrahedron Lett 2000;41:2239-2242.
3. Al-Sehemi AG, Atkinson RS, Fawcett J, Russell DR. 3-Di-[(S)-2- acetoxypropanoyl]aminoquinazolin-4(3H)-ones: stereostructure and application in kinetic resolution of amines. Tetrahedron Lett 2000;41:2243-2246.
4. Ie Y, Fu GC. A new benchmark for the non-enzymatic acylation of amines: use of a planar-chiral derivative of 4-pyrrolidinopyridine as the acylating agent. Chem Commun 2000;119-120.
5. Arai S, Bellemin-Laponnaz S, Fu GC. Kinetic resolution of amines by a non-enzymatic acylation catalyst. Angew Chem Int Ed 2001;40:234-236.
6. Arseniyadis S, Valleix A, Wagner A, Mioskowski C. Kinetic resolution of amines: a highly enantioselective and chemoselective acetylating agent with a unique solvent-induced reversal of stereoselectivity. Angew Chem Int Ed 2004;43:3314-3317.
7. Jones DS, Kenner GW, Preston J, Sheppard RC. Peptides. Part XVII. Synthesis of peptides and polymers of some sterically hindered amino acids via oxazolone intermediates. J Chem Soc 1965;6227-6239.
8. Kemp DS. Racemization in peptide synthesis. In: Gross E, Meienhofer J, editors. The peptides: analysis, synthesis, biology. New York: Academic Press; 1979. Vol 1, p 315-383.
9. Weygand F, Steglich W, Barocio de la Lama X. Über der sterichen Verlauf der Reaktion von Oxazolonen-(5) mit Aminosaüreestern. Tetrahedron 1966;22(Suppl 8, Pt I):9-13.
10. Frauendorfer E, Steglich W, Weygand F. Asymmetrische Synthesen mit 2-(Trifluoromethyl)-3-oxazolin-5-onen. III. Synthese von N-Pivaloyl-L-tert- leucyl-L-valin, einen Acyl-peptid mit hoher Gruppenhäufung. Chem Ber 1973;106:1019-1022.
11. Benoiton NL, Kuroda K, Chen FMF. The dependence of asymmetric induction on solvent polarity and temperature in peptide synthesis. Tetrahedron Lett 1981;22:3361-3364.
12. Miyazawa T, Otomatsu T, Higashi K, Yamada T, Kuwata S. Asymmetric induction during aminolysis of 5(4H)-oxazolones from N-benzoyl amino acids: almost specific formation of an epimer in the reaction of the oxazolone from N-benzoyl-DL-t-leucine with methyl-L-prolinate. Bull Chem Soc Jpn 1988;61:4161-4163.
13. Kresnov VP, Zhdanova EA, Solieva NZ, Sadretdinova LS, Bukrina IM, Demin AM, Levit GL, Ezhikova MA, Kodess MI. Study of the effect of the nature of the side chain in esters of α-amino acids on the diastereoselectivity in the synthesis of dipeptides with N-terminal N-acetylphenylalanine. Russ Chem Bull Int Ed 2004;53:1331-1334.
14. Calmes M, Glot C, Michel T, Rolland M, Martinez J. Dynamic kinetic resolution of racemic N-phthalyl amino acids using (S)-α- methylpantolactone as the chiral auxiliary. Tetrahedron: Asymmetry 2000;11:737-741.
15. α-tetrasubstituted α-amino acids. In: Goodman M, Felix A, Moroder L, Toniolo C, editors. Houben-Weyl methods of organic synthesis. Stuttgart: Thieme; 2003. Vol E22c, p 292-310.
16. Gatos M, Formaggio F, Crisma M, Toniolo C, Bonora GM, Benedetti E, Di Blasio B, Iacovino R, Santini A, Saviano M, Kamphuis J. Conformational characterization of the 1-aminocyclobutane-1-carboxylic acid residue in model peptides. J Pept Sci 1997;3:110-122.
17. 7c). J Chem Soc Perkin Trans 2 1997;2023-2032.
18. 11c). J Pept Sci 2000;6:571-583.
19. α-methylated α-amino acid side-chain on peptide preferred conformation. Biopolymers (Pept Sci) 1996;40:523-527.
20. α-methylation in the second position. Tetrahedron: Asymmetry 1997;8:1305-1314.
21. α-Methyl phenylglycine-based semisynthetic ampicillin and cephalexin analogues. Lett Pept Sci 1998;5:43-48.
22. α- phenylglycine peptides: a structural study. Lett Pept Sci 1998;5:223-225.
23. α-methyl phenylglycine as hosts in inclusion resolutions. Tetrahedron: Asymmetry 2004;15:1919-1927.
24. α-tetrasubstituted α-amino acids. J Org Chem 2004;69:3849-3856.
25. α-tetrasubstitution) . Biopolymers (Pept Sci) 2001;60:396-419.
26. Karle IL, Balaram P. Structural characteristics of α-helical peptide molecules containing Aib residues. Biochemistry 1990;29:6747-6756.
27. Leplawy MT, Jones DS, Kenner GW, Sheppard RC. Peptides. XI. Synthesis of peptides derived from α-methylalanine. Tetrahedron 1960; 11:39-51.
28. Valle G, Formaggio F, Crisma M, Bonora GM, Toniolo C, Bavoso A, Benedetti E, Di Blasio B, Pavone V, Pedone C. Linear oligopeptides. Part 147. Chemical and crystallographic study of the reaction between benzyloxycarbonyl chloride and α-aminoisobutyric acid. J Chem Soc Perkin Trans II 1986;1371-1376.
29. Sheldrick GM. SHELXS 97. Program for the solution of crystal structures. Göttingen, Germany: University of Göttingen; 1997.
30. Sheldrick GM. SHELXL 97. Program for the refinement of crystal structures. Göttingen, Germany: University of Göttingen; 1997.
31. Sonke T, Kaptein B, Boesten WHJ, Broxterman QB, Kamphuis J, Formaggio F, Toniolo C, Rutjes FPJT, Schoemaker HE. Amino-amidase-catalysed preparation and further transformations of enantiopure α-hydrogen- and α,α-disubstituted α-amino acids. In: Patel RN, editor. Stereoselective biocatalysis. New York: Dekker; 2000. p 23-58.
32. Carpino LA. 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive. J Am Chem Soc 1993;115:4397-4398.
33. Venkatachalam CM. Stereochemical criteria for polypeptides and proteins. V. Conformation of a system of three-linked peptide units. Biopolymers 1968;6:1425-1436.
34. Toniolo C. Intramolecularly hydrogen-bonded peptide conformations. CRC Crit Rev Biochem 1980;9:1-44.
35. Rose GD, Gierasch LM, Smith JP. Turns in peptides and proteins. Adv Protein Chem 1985;37:1-109.
36. Bonora GM, Mapelli C, Toniolo C, Wilkening RR, Stevens ES. Conformation analysis of linear peptides. 5. Spectroscopic characterization of β-turns in Aib-containing oligopeptides in chloroform. Int J Biol Macromol 1984;6:179-188.
37. IUPAC-IUB Commission on Biochemical Nomenclature. Abbreviations and symbols for the description of the conformation of polypeptide chains. Biochemistry 1970;9:3471-3479.
38. Ramakrishnan C, Prasad N. Study of hydrogen bonds in amino acids and peptides. Int J Protein Res 1971;3:209-231.
39. Taylor R, Kennard O, Versichel W. The geometry of the N-H⋯O=C hydrogen bond. 3. Hydrogen-bond distances and angles. Acta Crystallogr 1984;B40:280-288.
40. Görbitz CH. Hydrogen-bond distances and angles in the structures of amino acids and peptides. Acta Crystallogr 1989;B45:390-395.
41. α-methylated α-amino acids and the homochirality of life: searching for a link. Angew Chem Int Ed 2004;43:6695-6699.