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For recent reviews on the preparation of peptides and proteins having nonproteinogenic amino acid(s) or post-translational modification, see: (a) Muralidharan. V.; Muir, T. W. Nat. Methods 2006, 3, 429;
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(b) Nakagawa, S.; Tamakashi, Y.; Hamana, T.: Kawase, M.; Taketomi, S.; Ishibashi, Y.; Nishimura. O.; Fukuda, T. J. Am. Chem. Soc. 1994, 116, 5513;
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Nishimura, O.; Moriya, T.; Suenaga, M.; Tanaka, Y.; Itoh, T.; Koyama, N.; Fujii, R.; Hinuma, S.; Kitada, C.; Fujino, M. Chem. Pharm. Bull. 1998, 46, 1490;
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(e) Suenaga, M.; Itoh. T.; Miwa, M.; Koyama, N.; Hinuma. S.; Kitada, C.; Nishimura, O.; Fujino, M. J. Chem. Soc., Perkin Trans. 1 2000,1183;
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(f) Itoh, T.; Miwa, M.; Suenaga, M.; Ohtaki, T.: Kitada, C.; Nishimura, O.; Fujino, M. J. Chem. Soc. Perkin Trans. 1 2000, 1333;
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(g) Nishimura, O.; Suenaga, M.: Yamada, T.; Itoh, T.: Koyama, N.; Wakimasu. M.; Ohtaki, T.; Kitada, C.; Fujino, M. J. Chem. Soc., Perkin Trans. 1 2001, 1748;
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(h) Qi, J.: Wu. J.; Somkuti, G. A.; Watson, J. T. Biochemistry 2001, 40, 4531.
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Yamamoto, A.7
Kiso, Y.8
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20
-
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85031246454
-
-
Other side reactions including dimerization of the peptides by disulfide bond formation were also observed
-
Other side reactions including dimerization of the peptides by disulfide bond formation were also observed.
-
-
-
-
21
-
-
0023109951
-
-
The cyclic imide formation with concomitant peptide bond cleavage in neutral and basic conditions was previously reported: (a)
-
The cyclic imide formation with concomitant peptide bond cleavage in neutral and basic conditions was previously reported: (a) Geiger, T.: Clarke, S. J. Biol. Chem. 1987, 262, 785;
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(1987)
J. Biol. Chem.
, vol.262
, pp. 785
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Geiger, T.1
Clarke, S.2
-
23
-
-
0031799735
-
-
The ε-lactam formation accompanying amide bond cleavage was previously reported: (a)
-
The ε-lactam formation accompanying amide bond cleavage was previously reported: (a) Takenawa, T.; Oda, Y.; Ishihama, Y.; Iwakura, M. J. Biochem. 1998. 123, 1137;
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(1998)
J. Biochem.
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Takenawa, T.1
Oda, Y.2
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Iwakura, M.4
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24
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0033597333
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(b) Ishihama, Y.; Ito, O.; Oda, Y.; Takenawa, T.; Iwakura, M. Tetrahedron Lett. 1999, 40, 3415.
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Tetrahedron Lett.
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Ishihama, Y.1
Ito, O.2
Oda, Y.3
Takenawa, T.4
Iwakura, M.5
-
25
-
-
85031244352
-
-
A small amount of a β-elimination product was observed under the various cleavage conditions examined
-
A small amount of a β-elimination product was observed under the various cleavage conditions examined.
-
-
-
-
26
-
-
0037119022
-
-
Otaka, A.; Nakamura, M.; Nameki, D.; Kodama, E.; Uchiyama, S.; Nakamura, S.; Nakano, H.; Tamamura, H.: Kobayashi, Y.; Matsuoka, M.; Fujii, N. Angew. Chem., Int. Ed. 2002, 41, 2937.
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Angew. Chem., Int. Ed.
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Otaka, A.1
Nakamura, M.2
Nameki, D.3
Kodama, E.4
Uchiyama, S.5
Nakamura, S.6
Nakano, H.7
Tamamura, H.8
Kobayashi, Y.9
Matsuoka, M.10
Fujii, N.11
-
27
-
-
85031239377
-
-
Only partial S-cyanylations of two Cys residues in thioredoxin were observed. This was also verified by the recovery of C-termlnal capped thioredoxin 24a, b after basic treatment in the next step
-
Only partial S-cyanylations of two Cys residues in thioredoxin were observed. This was also verified by the recovery of C-termlnal capped thioredoxin 24a, b after basic treatment in the next step.
-
-
-
-
28
-
-
85031240012
-
-
Peptides 20a, b from 22a, b were identical to the authentic samples, which were obtained by the cleavage reaction of the synthetic peptides
-
Peptides 20a, b from 22a, b were identical to the authentic samples, which were obtained by the cleavage reaction of the synthetic peptides.
-
-
-
-
29
-
-
85031236142
-
-
Cytotoxicity of peptides 20a, b was not observed even at 10 uM in MAGI assay
-
Cytotoxicity of peptides 20a, b was not observed even at 10 uM in MAGI assay.
-
-
-
-
30
-
-
85031263412
-
-
The presence of a hydrolyzed ring-opening product indicates that the degradation presumably began with hydrolysis of the C-terminal aspartimide, Ref. 9
-
The presence of a hydrolyzed ring-opening product indicates that the degradation presumably began with hydrolysis of the C-terminal aspartimide, Ref. 9.
-
-
-
-
31
-
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0034744423
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(a) Kodama, E. I.; Kohgo, S.; Kitano, K.; Machida, H.; Gatanaga, H.; Shigeta, S.; Matsuoka, M.; Ohrui, H.; Mitsuya, H. Antimlcrob. Agents Chemother. 2001, 45. 1539;
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, pp. 1539
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Kohgo, S.2
Kitano, K.3
Machida, H.4
Gatanaga, H.5
Shigeta, S.6
Matsuoka, M.7
Ohrui, H.8
Mitsuya, H.9
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32
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0031948662
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(b) Maeda, Y.; Venzon, D. J.; Mitsuya, H. J. Infect. Dis. 1998, 177, 1207.
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