-
1
-
-
16244416275
-
-
H. Mihara, Y. Haruta, S. Sakamoto, N. Nishino, and H. Aoyagi, Chem. Lett., 1996, 1.
-
Chem. Lett.
, vol.1996
, pp. 1
-
-
Mihara, H.1
Haruta, Y.2
Sakamoto, S.3
Nishino, N.4
Aoyagi, H.5
-
2
-
-
0030529734
-
-
H. Mihara, K. Tomizaki, T. Fujimoto, S. Sakamoto, H. Aoyagi, and N. Nishino, Chem. Lett., 1996, 187.
-
Chem. Lett.
, vol.1996
, pp. 187
-
-
Mihara, H.1
Tomizaki, K.2
Fujimoto, T.3
Sakamoto, S.4
Aoyagi, H.5
Nishino, N.6
-
3
-
-
0028890586
-
-
D. R. Benson, B. R. Hart, X. Zhu, and M. B. Doughty, J. Am. Chem. Soc., 117, 8502 (1995).
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 8502
-
-
Benson, D.R.1
Hart, B.R.2
Zhu, X.3
Doughty, M.B.4
-
4
-
-
0028142931
-
-
C. T. Choma, K. Kaestle, K. S. Åkerfeldt, R. M. Kim, J. T. Groves, and W. F. DeGrado, Tetrahedron Lett., 35, 6191 (1994).
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 6191
-
-
Choma, C.T.1
Kaestle, K.2
Åkerfeldt, K.S.3
Kim, R.M.4
Groves, J.T.5
DeGrado, W.F.6
-
5
-
-
85022457076
-
-
K. S. Åkerfeldt, R. M. Kim, D. Camac, J. T. Groves, J. D. Lear, and W. F. DeGrado, J. Am. Chem. Soc., 114, 9656 (1992).
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 9656
-
-
Åkerfeldt, K.S.1
Kim, R.M.2
Camac, D.3
Groves, J.T.4
Lear, J.D.5
DeGrado, W.F.6
-
6
-
-
0000596816
-
-
T. Aral, K. Kobata, H. Mihara, T. Fujimoto, and N. Nishino, Bull. Chem. Soc. Jpn., 68, 1989 (1995); H. Mihara, N. Nishino, R. Hasegawa, and T. Fujimoto, Chem. Lett., 1992, 1805.
-
(1995)
Bull. Chem. Soc. Jpn.
, vol.68
, pp. 1989
-
-
Aral, T.1
Kobata, K.2
Mihara, H.3
Fujimoto, T.4
Nishino, N.5
-
7
-
-
0001885242
-
-
T. Aral, K. Kobata, H. Mihara, T. Fujimoto, and N. Nishino, Bull. Chem. Soc. Jpn., 68, 1989 (1995); H. Mihara, N. Nishino, R. Hasegawa, and T. Fujimoto, Chem. Lett., 1992, 1805.
-
Chem. Lett.
, vol.1992
, pp. 1805
-
-
Mihara, H.1
Nishino, N.2
Hasegawa, R.3
Fujimoto, T.4
-
10
-
-
0030974713
-
-
P. A. Arnold, W. R. Shelton, and D. R. Benson, J. Am. Chem. Soc., 119, 3181 (1997).
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 3181
-
-
Arnold, P.A.1
Shelton, W.R.2
Benson, D.R.3
-
11
-
-
0001305475
-
-
S. Sakamoto, S. Sakurai, A. Ueno, and H. Mihara, Chem. Commun., 1997, 1221.
-
Chem. Commun.
, vol.1997
, pp. 1221
-
-
Sakamoto, S.1
Sakurai, S.2
Ueno, A.3
Mihara, H.4
-
12
-
-
0028281579
-
-
D. E. Robertson, R. S. Farid, C. C. Moser, J. L. Urbauer, S. E. Mulholland, R. Pidikiti, J. D. Lear, A. J. Wand, W. F. DeGrado, and P. L. Dutton, Nature, 368, 425 (1994).
-
(1994)
Nature
, vol.368
, pp. 425
-
-
Robertson, D.E.1
Farid, R.S.2
Moser, C.C.3
Urbauer, J.L.4
Mulholland, S.E.5
Pidikiti, R.6
Lear, J.D.7
Wand, A.J.8
DeGrado, W.F.9
Dutton, P.L.10
-
13
-
-
0028154527
-
-
C. T. Choma, J. D. Lear, M. J. Nelson, P. L. Dutton, D. E. Robertson, and W. F. DeGrado, J. Am. Chem. Soc., 116, 856 (1994).
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 856
-
-
Choma, C.T.1
Lear, J.D.2
Nelson, M.J.3
Dutton, P.L.4
Robertson, D.E.5
DeGrado, W.F.6
-
14
-
-
0030066841
-
-
F. Rabanal, W. F. DeGrado, and P. L. Dutton, J. Am. Chem. Soc., 118, 473 (1996).
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 473
-
-
Rabanal, F.1
Degrado, W.F.2
Dutton, P.L.3
-
15
-
-
0030814567
-
-
T. B. Karpishin, T. A. Vannelli, and K. J. Glover, J. Am. Chem. Soc., 119, 9063 (1997).
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 9063
-
-
Karpishin, T.B.1
Vannelli, T.A.2
Glover, K.J.3
-
16
-
-
0028838508
-
-
J. Morais, P. N. Palma, C. Frazão, J. Caldeira, J. LeGall, I. Moura, J. J. G. Moura, and M. A. Carrondo, Biochemistry, 34, 12830 (1995).
-
(1995)
Biochemistry
, vol.34
, pp. 12830
-
-
Morais, J.1
Palma, P.N.2
Frazão, C.3
Caldeira, J.4
LeGall, J.5
Moura, I.6
Moura, J.J.G.7
Carrondo, M.A.8
-
17
-
-
0030611275
-
-
N. Igarashi, H. Moriyama, T. Fujiwara, Y. Fukumori, and N. Tanaka, Nature Struct. Biol., 4, 276 (1997).
-
(1997)
Nature Struct. Biol.
, vol.4
, pp. 276
-
-
Igarashi, N.1
Moriyama, H.2
Fujiwara, T.3
Fukumori, Y.4
Tanaka, N.5
-
18
-
-
0029637583
-
-
G. McDermott, S. M. Prince, A. A. Freer, A. M. Hawthornthwaite-Lawless, M. Z. Papiz, R. J. Cogdell, and N. W. Isaacs, Nature, 374, 517 (1995).
-
(1995)
Nature
, vol.374
, pp. 517
-
-
McDermott, G.1
Prince, S.M.2
Freer, A.A.3
Hawthornthwaite-Lawless, A.M.4
Papiz, M.Z.5
Cogdell, R.J.6
Isaacs, N.W.7
-
19
-
-
0018333224
-
-
B. W. Matthews, R. E. Fenna, M. C. Bolognesi, M. F. Schmid, and J. M. Olson, J. Mol. Biol., 131, 259 (1979).
-
(1979)
J. Mol. Biol.
, vol.131
, pp. 259
-
-
Matthews, B.W.1
Fenna, R.E.2
Bolognesi, M.C.3
Schmid, M.F.4
Olson, J.M.5
-
20
-
-
0022348605
-
-
J. Deisenhofer, O. Epp, K. Miki, R. Huber, and H. Michel, Nature, 318, 618 (1985).
-
(1985)
Nature
, vol.318
, pp. 618
-
-
Deisenhofer, J.1
Epp, O.2
Miki, K.3
Huber, R.4
Michel, H.5
-
21
-
-
0013631129
-
-
M. Ushiyama, Y. Katayama, and T. Yamamura, Chem. Lett., 1995, 395.
-
Chem. Lett.
, vol.1995
, pp. 395
-
-
Ushiyama, M.1
Katayama, Y.2
Yamamura, T.3
-
22
-
-
0001602005
-
-
J. P. Collman, J. I. Brauman, K. M. Doxsee, T. R. Halbert, E. Bunnenberg, R. E. Linder, G. N. LaMar, J. D. Gaudio, G. Lang, and K. Spartalian, J. Am. Chem. Soc., 102, 4182 (1980).
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 4182
-
-
Collman, J.P.1
Brauman, J.I.2
Doxsee, K.M.3
Halbert, T.R.4
Bunnenberg, E.5
Linder, R.E.6
LaMar, G.N.7
Gaudio, J.D.8
Lang, G.9
Spartalian, K.10
-
23
-
-
0033474897
-
-
M. Ushiyama, F. Arisaka, and T. Yamamura, Chem. Lett., 1999, 127.
-
Chem. Lett.
, vol.1999
, pp. 127
-
-
Ushiyama, M.1
Arisaka, F.2
Yamamura, T.3
-
24
-
-
0016856701
-
-
J. P. Collman, R. R. Gagne, C. A. Reed, T. R. Halbert, G. Lang, and W. T. Robinson, J. Am. Chem. Soc., 97, 1427 (1975).
-
(1975)
J. Am. Chem. Soc.
, vol.97
, pp. 1427
-
-
Collman, J.P.1
Gagne, R.R.2
Reed, C.A.3
Halbert, T.R.4
Lang, G.5
Robinson, W.T.6
-
26
-
-
0002330492
-
-
ed by G. D. Fasman, Plenum Press, New York
-
P. Prevelige, Jr., and G. D. Fasman, "Prediction of Protein Structure and the Principles of Protein Conformation," ed by G. D. Fasman, Plenum Press, New York (1989), pp. 391-416.
-
(1989)
Prediction of Protein Structure and the Principles of Protein Conformation
, pp. 391-416
-
-
Prevelige P., Jr.1
Fasman, G.D.2
-
28
-
-
0013577319
-
-
note
-
2, from which the stabilization free energy on the ice-shell liquidation was derived according to Ref. 26.
-
-
-
-
29
-
-
0013576661
-
-
note
-
The detail will be reported elsewhere.
-
-
-
-
30
-
-
0023977089
-
-
Molecular graphics images were produced using the MidasPlus software system from the Computer Graphics Laboratory, University of California, San Francisco: T. E. Ferrin, C. C. Huang, L. E. Jarvis, and R. Langridge, J. Mol. Graphics, 6, 13 (1988).
-
(1988)
J. Mol. Graphics
, vol.6
, pp. 13
-
-
Ferrin, T.E.1
Huang, C.C.2
Jarvis, L.E.3
Langridge, R.4
-
31
-
-
84988053694
-
-
S. J. Weiner, P. A. Kollman, D. T. Nguyen, and D. A. Case, J. Comput. Chem., 27, 230 (1986).
-
(1986)
J. Comput. Chem.
, vol.27
, pp. 230
-
-
Weiner, S.J.1
Kollman, P.A.2
Nguyen, D.T.3
Case, D.A.4
-
32
-
-
0013627692
-
-
note
-
Due to its impossibility of purification of intermediates, the solid-phase peptide synthesis is inferior to the liquid phase method to make sure the preparation of high purity product (Ref. 24). Furthermore, the purification of protected peptide is generally difficult because of its low solubility (Ref. 32), even if the peptide is carefully cleaved from the resin without deprotection of the side chains.
-
-
-
-
34
-
-
37049125907
-
-
G. C. Stelakatos, A. Paganou, and L. Zervas, J. Chem. Soc. C, 1966, 1191.
-
J. Chem. Soc. C
, vol.1966
, pp. 1191
-
-
Stelakatos, G.C.1
Paganou, A.2
Zervas, L.3
-
35
-
-
0013606807
-
-
note
-
2N-n, for the phenacyl and Boc cleaved forms, respectively, where n means the substance number 1 to 6. For example, 6-OH equals Boc-Glu(OBzl)-Glu(OBzl)-Ala-Leu-Glu(OBzl)-Lys-(ClZ)-His-Glu(OBzl)-Lys(ClZ)-Ala- Leu-Glu(OBzl)-Lys-(ClZ)-His-Glu(OBzl)-Lys(ClZ)-OH.
-
-
-
-
36
-
-
37049098813
-
-
D. L. Nguyen, R. Seyer, A. Heitz, and B. Castro, J. Chem. Soc., Perkin Trans. I, 1985, 1025.
-
J. Chem. Soc., Perkin Trans. I
, vol.1985
, pp. 1025
-
-
Nguyen, D.L.1
Seyer, R.2
Heitz, A.3
Castro, B.4
-
37
-
-
0013576662
-
-
note
-
4, the application of Zn powder caused a fast remarkable bleaching of this compound.
-
-
-
-
38
-
-
0023386969
-
-
N. Fujii, A. Otaka, O. Ikemura, M. Hatano, A. Okamachi, S. Funakoshi, M. Sakurai, T. Shioiri, and H. Yajima, Chem. Pharm. Bull., 35, 3447 (1987).
-
(1987)
Chem. Pharm. Bull.
, vol.35
, pp. 3447
-
-
Fujii, N.1
Otaka, A.2
Ikemura, O.3
Hatano, M.4
Okamachi, A.5
Funakoshi, S.6
Sakurai, M.7
Shioiri, T.8
Yajima, H.9
-
39
-
-
37049081050
-
-
N. Fujii, A. Otaka, O. Ikemura, K. Akaji, S. Funakoshi, Y. Hayashi, Y. Kuroda, and H. Yajima, J. Chem. Soc., Chem. Commun., 1987, 274.
-
J. Chem. Soc., Chem. Commun.
, vol.1987
, pp. 274
-
-
Fujii, N.1
Otaka, A.2
Ikemura, O.3
Akaji, K.4
Funakoshi, S.5
Hayashi, Y.6
Kuroda, Y.7
Yajima, H.8
-
40
-
-
0000088993
-
-
T. Fujii, T. Kimura, and S. Sakakibara, Bull. Chem. Soc. Jpn., 49, 1595 (1976).
-
(1976)
Bull. Chem. Soc. Jpn.
, vol.49
, pp. 1595
-
-
Fujii, T.1
Kimura, T.2
Sakakibara, S.3
-
41
-
-
0022541453
-
-
N. Fujii, M. Sakurai, K. Akaji, M. Nomizu, H. Yajima, K. Mizuta, M. Aono, M. Moriga, K. Inoue, R. Hosotani, and T. Tobe, Chem. Pharm. Bull., 34, 2397 (1986).
-
(1986)
Chem. Pharm. Bull.
, vol.34
, pp. 2397
-
-
Fujii, N.1
Sakurai, M.2
Akaji, K.3
Nomizu, M.4
Yajima, H.5
Mizuta, K.6
Aono, M.7
Moriga, M.8
Inoue, K.9
Hosotani, R.10
Tobe, T.11
-
42
-
-
0025347972
-
-
R. Seyer, A. Aumelas, A. Caraty, P. Rivaille, and B. Castro, Int. J. Peptide Protein Res., 35, 465 (1990).
-
(1990)
Int. J. Peptide Protein Res.
, vol.35
, pp. 465
-
-
Seyer, R.1
Aumelas, A.2
Caraty, A.3
Rivaille, P.4
Castro, B.5
-
43
-
-
0019843623
-
-
T. Kimura, M. Takai, Y. Masui, T. Morikawa, and S. Sakakibara, Biopolymers, 20, 1823 (1981).
-
(1981)
Biopolymers
, vol.20
, pp. 1823
-
-
Kimura, T.1
Takai, M.2
Masui, Y.3
Morikawa, T.4
Sakakibara, S.5
-
44
-
-
0019257339
-
-
P. Rivaille, J. P. Gautron, B. Castro, and G. Milhaud, Tetrahedron, 36, 3413 (1980).
-
(1980)
Tetrahedron
, vol.36
, pp. 3413
-
-
Rivaille, P.1
Gautron, J.P.2
Castro, B.3
Milhaud, G.4
-
45
-
-
0025132866
-
-
C-B. Xue, A. Ewenson, J. M. Becker, and F. Naider, Int. J. Peptide Protein Res., 36, 362 (1990).
-
(1990)
Int. J. Peptide Protein Res.
, vol.36
, pp. 362
-
-
Xue, C.-B.1
Ewenson, A.2
Becker, J.M.3
Naider, F.4
-
46
-
-
0013579274
-
-
note
-
The phenacyl esters of 1,4,5, and 6 were efficiently removed by Zn/90% acetic acid.
-
-
-
-
47
-
-
0013612009
-
-
note
-
a) This side reaction gave only one by-product which showed the same mass number as 6, which shows the possibility of the racemization of 6 at the coupling.
-
-
-
-
48
-
-
0013579275
-
-
note
-
b) Histidine easily racemizes via the steric interaction of the imidazole group and the carboxyl group, or the elimination of the a-hydrogen by the imidazole group (Refs. 47 and 48). The molecular modeling of peptide fragments 3-OH and 5-OH showed that the imidazole groups of their histidines, which are placed on the third residues from the carboxyl termini, can take close positions to their C-terminal amino acids, which might cause the similar racemization effect on the C-terminal residues.
-
-
-
-
50
-
-
0013604476
-
-
ed by E. Gross and J. Meienhofer, Academic Press, New York
-
G. Barany and R. B. Merrifield, "The Peptides: Analysis, Synthesis, Biology," ed by E. Gross and J. Meienhofer, Academic Press, New York (1979), Vol. 2, pp. 179-189.
-
(1979)
The Peptides: Analysis, Synthesis, Biology
, vol.2
, pp. 179-189
-
-
Barany, G.1
Merrifield, R.B.2
-
52
-
-
0000977998
-
-
L. A. Carpino, A. EI-Faham, C. A. Minor, and F. Albericio, J. Chem. Soc., Chem. Commun., 1994, 201.
-
J. Chem. Soc., Chem. Commun.
, vol.1994
, pp. 201
-
-
Carpino, L.A.1
Ei-Faham, A.2
Minor, C.A.3
Albericio, F.4
-
53
-
-
0013606809
-
-
note
-
80% yield was achieved at this point.
-
-
-
-
54
-
-
85007757234
-
-
B. Castro, J.-R. Dormoy, B. Dourtoglou, G. Evin, and C. Selve, J-C. Ziegler, Synthesis, 1976, 751.
-
Synthesis
, vol.1976
, pp. 751
-
-
Castro, B.1
Dormoy, J.-R.2
Dourtoglou, B.3
Evin, G.4
Selve, C.5
Ziegler, J.-C.6
-
55
-
-
0025014627
-
-
J. Coste, D. Le-Nguyen, and B. Castro, Tetrahedron Lett., 31, 205 (1990).
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 205
-
-
Coste, J.1
Le-Nguyen, D.2
Castro, B.3
-
56
-
-
0013607579
-
-
note
-
The aqueous acetonitrile solution containing TEA or AcOH achieved good separation, but the TEA-containing eluent also achieved a good result with less amount of water. This was advantageous to treat the compound, because the mixing of water decreased the solubility of compound.
-
-
-
-
59
-
-
0001601397
-
-
R. A. Freitag, J. A. Mercer-Smith, and D. G. Whitten, J. Am. Chem. Soc., 103, 1226 (1981).
-
(1981)
J. Am. Chem. Soc.
, vol.103
, pp. 1226
-
-
Freitag, R.A.1
Mercer-Smith, J.A.2
Whitten, D.G.3
-
60
-
-
0013627504
-
-
note
-
In the presence of 6-OH, such instability of the porphyrin fragment was not observed.
-
-
-
-
61
-
-
0000880719
-
-
Y. Ohtsu, Y. Shiojima, T. Okumura, J. Koyama, K. Nakamura, O. Nakata, K. Kimata, and N. Tanaka, J. Chromatogr., 481, 147 (1989).
-
(1989)
J. Chromatogr.
, vol.481
, pp. 147
-
-
Ohtsu, Y.1
Shiojima, Y.2
Okumura, T.3
Koyama, J.4
Nakamura, K.5
Nakata, O.6
Kimata, K.7
Tanaka, N.8
-
62
-
-
0010376670
-
-
J. Koyama, J. Nomura, Y. Ohtsu, O. Nakata, and M. Takahashi, Chem. Lett., 1990, 687.
-
Chem. Lett.
, vol.1990
, pp. 687
-
-
Koyama, J.1
Nomura, J.2
Ohtsu, Y.3
Nakata, O.4
Takahashi, M.5
-
63
-
-
0030567341
-
-
A. Cammers-Goodwin, T. J. Allen, S. L. Oslick, K. F. McClure, J. H. Lee, and D. S. Kemp, J. Am. Chem. Soc., 118, 3082 (1996).
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 3082
-
-
Cammers-Goodwin, A.1
Allen, T.J.2
Oslick, S.L.3
McClure, K.F.4
Lee, J.H.5
Kemp, D.S.6
-
64
-
-
0013606811
-
-
note
-
-1 (Ref. 63).
-
-
-
-
65
-
-
0026018050
-
-
P. C. Lyu, J. C. Sherman, A. Chen, and N. R. Kallenbach, Proc. Natl. Acad. Sci. U.S.A., 88, 5317 (1991).
-
(1991)
Proc. Natl. Acad. Sci. U.S.A.
, vol.88
, pp. 5317
-
-
Lyu, P.C.1
Sherman, J.C.2
Chen, A.3
Kallenbach, N.R.4
-
66
-
-
0000562011
-
-
I. Hamachi, K. Nakamura, A. Fujita, and T. Kunitake, J. Am. Chem. Soc., 115, 4966 (1993).
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 4966
-
-
Hamachi, I.1
Nakamura, K.2
Fujita, A.3
Kunitake, T.4
-
67
-
-
0030659049
-
-
C. E. MacPhee, M. A. Perugini, W. H. Sawyer, and G. J. Howlett, FEBS Lett., 416, 265 (1997).
-
(1997)
FEBS Lett.
, vol.416
, pp. 265
-
-
MacPhee, C.E.1
Perugini, M.A.2
Sawyer, W.H.3
Howlett, G.J.4
-
68
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0013607070
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note
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1H NMR, FAB MS, and elemental analysis were reported in the Ref. 20.
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