Epimerization free synthesis of O-acyl isodipeptides employing COMU

Protein and Peptide Letters

Volumn 19, Issue 4, 2012, Pages 406-410

  Samarasimhareddy, M ^a   Hemantha, Hosahalli P ^a   Ananda, Kuppanna ^b   Sureshbabu, Vommina V ^a  

^a BANGALORE UNIVERSITY   (India)

^b Matrix Laboratories Limited   (India)

Author keywords

Click peptide; COMU; Difficult sequence; Esterification; O acyl isodipeptide

Indexed keywords

1 [(1 (CYANO 2 ETHOXY 2 OXOETHYLIDENEAMINOOXY)DIMETHYLAMINOMORPHOLINOMETHYLENE)METHANAMINIUM HEXAFLUOROPHOSPHATE]; DIPEPTIDE; O ACYL ISODIPEPTIDE; REAGENT; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL REACTION KINETICS; CHIRAL CHROMATOGRAPHY; EPIMERIZATION; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; SOLID PHASE SYNTHESIS;

EID: 84858832562     PISSN: 09298665     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986612799789413     Document Type: Article

References (20)

1. Sheppard, R. J. Pept. Sci. 2003, 9, 545-552
2. Coin, I.; Dolling, R.; Krause, E.; Bienert, M.; Beyermann, M.; Sferdean, C. D.; Carpino, L. A. Depsipeptide methodology for solid-phase peptide synthesis: circumventing side reactions and development of an automated technique via depsidipeptide units. J. Org. Chem. 2006, 71(16), 6171-6177 (Pubitemid 44200288)
3. Carpino, L. A.; Krause, E.; Sferdean, C. D.; Schumann, M.; Fabian, H.; Bienert, M.; Beyermann, M. Synthesis of 'difficult' peptide sequences: application of a depsipeptide technique to the Jung-Redemann 10-and 26-mers and the amyloid peptide A(1-42). Tetrahedron Lett. 2004, 45(40), 7519-7522.
4. Mutter, M.; Chandavarkar, A.; Boyat, C.; Lopez, J.; Santos, S. D.; Mandal, B.; Mimna, R.; Murat, K.; Patiny, L.; Saucede, L.; Tuchscherer, G. Switch peptides in statu nascendi: induction of conformational transitions relevant to degenerative diseases. Angew. Chem. Int. Ed., 2004, 43(32), 4172-4178 (Pubitemid 39257431)
5. Wohr, T.; Wahl, F.; Nefzi, A.; Rohwedder, B.; Sato, T.; Sun, X.; Mutter, M. Pseudo-prolines as a solubilizing, structure-disrupting protection technique in peptide synthesis. J. Am. Chem. Soc., 1996, 118(39), 9218-9227 (Pubitemid 26355114)
6. Johnson, T.; Quibell, M.; Owen, D.; Sheppard, R. C. A reversible protecting group for the amide bond in peptides. Use in the synthesis of 'difficult sequences'. J. Chem. Soc., Chem. Commun. 1993, 369-372.
7. Taniguchi, A.; Sohma, Y.; Kimura, M.; Okada, T.; Ikeda, K.; Hayashi, Y.; Kimura, T.; Hirota, S.; Matsuzaki, K.; Kiso, Y. Click Peptide" based on the "O-acyl isopeptide method": control of A142 production from a photo-triggered A142 analogue. J. Am. Chem. Soc. 2006, 128(3), 696-697 (Pubitemid 43153004)
8. Hentschel, J.; Krause, E.; Borner, H. G. Switch-Peptides to Trigger the Peptide Guided Assembly of Poly(ethylene oxide)Peptide Conjugates into Tape Structures. J. Am. Chem. Soc. 2006, 128(24), 7722-7723. (Pubitemid 43945699)
9. (Skwarczynski, M.; Sohma, Y.; Noguchi, M.; Kimura, T.; Hayashi, Y.; Kiso, Y. ON, Intramolecular alkoxycarbonyl migration of typical protective groups in hydroxyamino acids. J. Org. Chem. 2006, 71(6), 2542-2545
10. Sohma, Y.; Sasaki, M.; Hayashi, Y.; Kimura, T.; Kiso, Y. Novel and efficient synthesis of difficult sequence-containing peptides through O-N intramolecular acyl migration reaction of O-acyl isopeptides. Chem. Commun., 2004, 1, 124-125 (Pubitemid 38121992)
11. Sohma, Y.; Hayashi, Y.; Kimura, M.; Chiyomori, Y.; Taniguchi, A.; Sasaki, M.; Kimura, T.; Kiso, Y. The 'O-acyl isopeptide method' for the synthesis of difficult sequencecontaining peptides: application to the synthesis of Alzheimer's disease-related amyloid peptide (A) 1-42. J. Pept. Sci. 2005, 11(8), 441-451. (Pubitemid 41086924)
12. Sohma, Y.; Kiso, Y. "Click peptides"-chemical biology-oriented synthesis of Alzheimer's disease-related amyloid peptide (A) analogues based on the "O-acyl isopeptide method". Chem Bio Chem 2006, 7, 1549-1557. (Pubitemid 44555999)
13. Sohma, Y.; Taniguchi, A.; Skwarczynski, M.; Yoshiya, T.; Fukao, F.; Kimura, T.; Hayashi, Y.; Kiso, Y. O-Acyl isopeptide method' for the efficient synthesis of difficult sequence-containing peptides: use of 'O-acyl isodipeptide unit. Tetrahedron Lett. 2006, 47(18), 3013-3017.
14. Yoshiya, T.; Taniguchi, A.; Sohma, Y.; Fukao, F.; Nakamura, S.; Abe, N.; Ito, N.; Skwarczynski, M.; Kimura, T.; Hayashi, Y.; Kiso, Y. "O-Acyl isopeptide method" for peptide synthesis: synthesis of forty kinds of "O-acyl isodipeptide unit" Boc-Ser/Thr(Fmoc-Xaa)-OH. Org. Biomol. Chem. 2007, 5(11), 1720-1730. (Pubitemid 46794162)
15. Lalithamba, H. S.; Hemantha, H. P.; Sureshbabu, V. V. Synthesis of oligo peptides through O-acyl isopeptide method. Protein Pept. Lett. 2011, 18, 848-857.
16. El-Faham, A.; Albericio, F. COMU: A third generation of uronium-type coupling reagents. J. Pept. Sci., 2010, 16(1), 6-9.
17. El-Faham, A.; Funosas, R. S.; Prohens, R.; Albericio, F. COMU: a safer and more effective replacement for benzotriazole-based uronium coupling reagents. Chem. Eur. J., 2009, 15(37), 9404-9416.
18. Subiros-Funosas, R.; Acosta, G. A.; El-Faham, A.; Albericio, F. Microwave irradiation and COMU: a potent combination for solidphase peptide synthesis. Tetrahedron Lett., 2009, 50(45), 6200-6202.
19. Tyrrell, E.; Brawn, P.; Carew, M.; Greenwood, I. An expedient conversion of -amino acids into Weinreb amides using COMU® as a coupling agent. Tetrahedron Lett., 2011, 52(3), 369-372.
20. Chiral-HPLC analyses were carried out employing Chiralpak IA, 250 x 4.6 mm, 5 μL (solvent-hexane:EtOH, 9:1; flow rate 1.0 mL/min).