A novel method for peptide block synthesis using unprotected peptides

Tetrahedron Letters

Volumn 40, Issue 17, 1999, Pages 3415-3418

  Ishihama, Yasushi ^a   Ito, Osamu ^a   Oda, Yoshiya ^a   Takenawa, Tatsuyuki ^b   Iwakura, Masahiro ^b  

^a EISAI CO LTD   (Japan)

^b NATL INST BIOSCI HUM TECHNOL   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE DERIVATIVE; PEPTIDE; SYNTHETIC PEPTIDE;

ARTICLE; CHEMICAL REACTION; MOLECULAR INTERACTION; PEPTIDE SYNTHESIS; STEREOCHEMISTRY;

EID: 0033597333     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00504-3     Document Type: Article

References (12)

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3. (3) Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779.
4. (4) Baca, M.; Muir, T. W.; Schnolzer, M.; Kent, S. B. H. J. Am. Chem. Soc. 1995, 117, 1881-1887.
5. (5) Rose, K. J. Am. Chem. Soc. 1994, 116, 30-33.
6. (6) Shao, J.; Tam, J. P. J. Am. Chem. Soc. 1995, 117, 3893-3899.
7. (7) Liu, C.; Rao, C.; Tam, J. P. J. Am. Chem. Soc. 1996, 118, 307-312.
8. (8) Catsimpoolas, N.; Wood, J. L. J. Biol. Chem. 1966, 241, 1790-1796.
9. (9) Jacobson, G. R.; Schaffer, M. H.; Stark, G. R.; Vanaman, T. C. J. Biol. Chem. 1973, 248, 6583-6591.
10. (10) Takenawa, T.; Oda, Y.; Ishihama, Y.; Iwakura, M. J. Biochem. 1998, 123, 1137-1144.
11. (11) A 10 μL aliquot of the reaction mixture was introduced into the LC/MS system. The LC separation was performed with an acetonitrile gradient containing 0.1 % TFA for an ODS column (150 × 2.1 mm i.d., 5 μm). The electrospray tip was held at a potential of 5000 V. The MS system was operated with an orifice voltage of 120 V and the scanning range was from 200 to 1500 m/z using a step size of 1.0 and a dwell time of 1 ms. Tandem MS spectra for determination of the peptide sequence were obtained as the averaged sum of 20 scans from 50 to 700 using a step size of 1.0 and dwell time of 10 ms with argon as the CID gas.
12. 1H-NMR data indicated that the Ac-AAK lactam has four peptide bonds, whereas Ac-AAK has three peptide bonds. Other data also confirmed the structure of the Ac-AAK lactam.