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1
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0024501805
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a) N Andres, H Wolf, H. Zahner, E. Rossner, A. Zeeck, W. A Konig, V. Sinnwell, Helv Chim Acta 1989, 72, 426-437,
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(1989)
Helv Chim Acta
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, pp. 426-437
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Andres, N.1
Wolf, H.2
Zahner, H.3
Rossner, E.4
Zeeck, A.5
Konig, W.A.6
Sinnwell, V.7
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2
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5444252964
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Eur Pat Appl. 1990 EP 385936 AI 19900905
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b) H Zahner, N. Andres, A Zeeck, E Rossner, H Wolf, W A Konig, V. Sinnwell, A Fredenhagen, Eur Pat Appl. 1990 EP 385936 AI 19900905,
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Zahner, H.1
Andres, N.2
Zeeck, A.3
Rossner, E.4
Wolf, H.5
Konig, W.A.6
Sinnwell, V.7
Fredenhagen, A.8
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4
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0012305750
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d) E Rossner, A Zeeck, W A. Konig, Angew Chem 1990, 102, 84-85, Angew Chem Int Ed Engl 1990, 29, 64-65
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(1990)
Angew Chem
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, pp. 84-85
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Rossner, E.1
Zeeck, A.2
Konig, W.A.3
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5
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0012318137
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d) E Rossner, A Zeeck, W A. Konig, Angew Chem 1990, 102, 84-85, Angew Chem Int Ed Engl 1990, 29, 64-65
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(1990)
Angew Chem Int Ed Engl
, vol.29
, pp. 64-65
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-
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6
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5444226799
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-
note
-
The previously unknown absolute configurations of the two nitrocyclopropylalanine residues as well as the 4-propenylproline moiety in 1 were established by a series of feeding experiments with the appropriate enantiomerically pure deuterium-labeled amino acids. It was additionally confirmed (in the case of 4-propenylproline) by a series of HPLC and HPLC/MS experiments
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-
-
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7
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5444223259
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For the synthesis of all four stereoisomers of 3-(trans-2- nitrocyclopropyl)alanine see. a) O. V Larionov, T F. Savelieva, K A Kochetkov, N. S Ikonnikov, S I Kozhushkov, D. S. Yufit, J A K Howard, V N Khrustalev, Yu N. Belokon, A de Meijere, Eur J Org. Chem 2003, 869-877
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(2003)
Eur J Org Chem
, pp. 869-877
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-
Larionov, O.V.1
Savelieva, T.F.2
Kochetkov, K.A.3
Ikonnikov, N.S.4
Kozhushkov, S.I.5
Yufit, D.S.6
Howard, J.A.K.7
Khrustalev, V.N.8
Belokon, Yu.N.9
De Meijere, A.10
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8
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-
0029059341
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-
for a partial elucidation of the relative and absolute configurations of the two 3-(trans-2-nitrocyclopropyl)alanine moieties in hormaomycm 1, and the synthesis of enantiomerically pure mixtures of epimers of 3-(trans-2- nitrocyclopropyl)alanine, see also b) J Zindel, A de Meijere, J. Org Chem. 1995, 60, 2968-2973,
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(1995)
J Org Chem
, vol.60
, pp. 2968-2973
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Zindel, J.1
De Meijere, A.2
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9
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0027416890
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c) J. Zindel, A Zeeck, W. A. Konig, A de Meijere, Tetrahedron Lett 1993, 54, 1917-1920
-
(1993)
Tetrahedron Lett
, vol.54
, pp. 1917-1920
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-
Zindel, J.1
Zeeck, A.2
Konig, W.A.3
De Meijere, A.4
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12
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0000770270
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L. A. Carpino, H G Chao, S Ghassemi, E M Mansour, C Riemer, R Warrass, D Sadat-Aalaee, G. A Truran, H Imazumi, A. El-Faham, D Ionescu, M Ismail, T L Kowaleski, C H. Han, H. Wenschuh, M. Beyermann, M Bienert, H Shroff, F Albericio, S. A Triolo, N. A. Sole, S. A Kates, J Org Chem 1995, 60, 7718-7719
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(1995)
J Org Chem
, vol.60
, pp. 7718-7719
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-
Carpino, L.A.1
Chao, H.G.2
Ghassemi, S.3
Mansour, E.M.4
Riemer, C.5
Warrass, R.6
Sadat-Aalaee, D.7
Truran, G.A.8
Imazumi, H.9
El-Faham, A.10
Ionescu, D.11
Ismail, M.12
Kowaleski, T.L.13
Han, C.H.14
Wenschuh, H.15
Beyermann, M.16
Bienert, M.17
Shroff, H.18
Albericio, F.19
Triolo, S.A.20
Sole, N.A.21
Kates, S.A.22
more..
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13
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5444275477
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note
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The relatively low yield must be attributed to the noticeable susceptibility of the MOM ester to nucleophilic attack by the free amino group, especially when formation of a diketopiperazine ring is possible.
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14
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5444224507
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note
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The tetrapeptide 13b can also be used towards the synthesis of various analogues of 1
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16
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5444260938
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Although several N-MeZ-acylated glycines were prepared as early as in 1951 (cf. D M Channing, P B Turner, G. T. Young, Nature 1951, 167, 487-488), the authors considered that "these compounds appear to offer little advantage over the corresponding carbobenzyloxy compounds"; to the best of our knowledge, the application of p-methylbenzyloxycarbonyl group for peptide synthesis has never been considered again
-
(1951)
Nature
, vol.167
, pp. 487-488
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Channing, D.M.1
Turner, P.B.2
Young, G.T.3
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17
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0028940130
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2O (cf.. E. C. Roos, P Bernabe, H Hiemstra, W. N Speckamp, B Kaptein, W H J Bosten, J Org. Chem 1995, 60, 1733-1740) gave an inseparable mixture of unreacted and transprotected peptides in 34% yield, although with model peptides this technique worked pretty well (90-100% yield of the desirable product)
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(1995)
J Org Chem
, vol.60
, pp. 1733-1740
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-
Roos, E.C.1
Bernabe, P.2
Hiemstra, H.3
Speckamp, W.N.4
Kaptein, B.5
Bosten, W.H.J.6
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18
-
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5444274274
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-
note
-
b) The ester bond between the (4-PE)Pro and a-Thr fragments may also be cleaved under strongly acidic (TFMSA in TFA, TMSOTf) conditions
-
-
-
-
19
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5444271504
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-
note
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c) For the model dipeptide MeZ-Phe-Val-OMe
-
-
-
-
20
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-
5444226167
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-
note
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d) From the secondary amino group of the (4-PE)Pro residue of the C-TMSE-protected acyclic precursor of the cyclic part of 1
-
-
-
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21
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5444253551
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-
note
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e) The rate of cleavage of the conventional Z-protective group was unacceptably slow even in the case of the model ester Z-Thr(OFmocPro)-OMe (incomplete deprotection with 20% thioanisole in TFA in 12 h at ambient temperature).
-
-
-
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22
-
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5444247613
-
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note
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f) The 3-methylbenzyloxycarbonyl and 3,5-dimethylbenzyloxycarbonyl groups were also tested, but turned out to be somewhat less suitable for application in this synthesis
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-
-
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23
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0030470879
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A Ehrlich, H U Heyne, R Winter, M Beyermann, H Haber, L A Carpino, M. Bienert, J Org Chem 1996, 61, 8831-8838.
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(1996)
J Org Chem
, vol.61
, pp. 8831-8838
-
-
Ehrlich, A.1
Heyne, H.U.2
Winter, R.3
Beyermann, M.4
Haber, H.5
Carpino, L.A.6
Bienert, M.7
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24
-
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5444221019
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-
note
-
a) Chpca-(3-Ncp)Ala-OH was also synthesized, but turned out to be too unstable to be used for condensation with the deprotected 17.
-
-
-
-
25
-
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5444237939
-
-
note
-
[9] reagent unexpectedly caused significant epimerization at the α-carbon of the (3-Ncp)Ala residue in the side chain and gave a separable mixture of epimers (MOM-1 and epi-MOM-1) in moderate yield
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-
-
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26
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0042751186
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S. Kim, I S Kee, Y. H. Park, J H. Park, Synlett 1991, 183-184
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(1991)
Synlett
, pp. 183-184
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-
Kim, S.1
Kee, I.S.2
Park, Y.H.3
Park, J.H.4
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27
-
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5444242334
-
-
note
-
a) The CD spectra were measured in methanol.
-
-
-
-
28
-
-
5444233941
-
-
note
-
b) It is noteworthy that both MOM-1 and epi-MOM-1 were equally active in this test and their activity was about 3 5 times lower than the activity of 1
-
-
-
-
29
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0030875121
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Compare K. Fujii, Y Ikai, T. Mayumi, H. Oka, M. Suzuki, K. Harada, Anal Chem 1997, 69, 3346-3352
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(1997)
Anal Chem
, vol.69
, pp. 3346-3352
-
-
Fujii, K.1
Ikai, Y.2
Mayumi, T.3
Oka, H.4
Suzuki, M.5
Harada, K.6
-
30
-
-
5444233330
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-
note
-
[1d] a mixture of all stereoisomers of 3-methylphenylalanine had been used as a reference). These latest results were in accordance with those obtained before.
-
-
-
-
32
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0001010190
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b) P. G. Anderson, D Guijaro, D. Tanner, J. Org Chem 1997, 62, 7364-7375
-
(1997)
J Org Chem
, vol.62
, pp. 7364-7375
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Anderson, P.G.1
Guijaro, D.2
Tanner, D.3
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33
-
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5444249535
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Patent US 5 580981, 1996
-
L. A. Carpino, Patent US 5 580981, 1996.
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Carpino, L.A.1
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36
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0001311213
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b) E. Nicolas, K C Russel, V J. Hruby, J Org Chem 1993, 58, 766-770
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(1993)
J Org Chem
, vol.58
, pp. 766-770
-
-
Nicolas, E.1
Russel, K.C.2
Hruby, V.J.3
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37
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0029075031
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D M Birney, D C Cole, C E Crosson, B F. Kahl, B. W Neff, T. W Reid, K Ren, R D. Walkup, J Med Chem 1995, 38, 2478-2482.
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(1995)
J Med Chem
, vol.38
, pp. 2478-2482
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Birney, D.M.1
Cole, D.C.2
Crosson, C.E.3
Kahl, B.F.4
Neff, B.W.5
Reid, T.W.6
Ren, K.7
Walkup, R.D.8
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