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2
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0002737999
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Chemical Synthesis of Peptides
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Oxford University Press New York
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Chemical Synthesis of Peptides S.M. Hecht Bioorganic Chemistry: Peptides and Proteins 1998 Oxford University Press New York 27 64
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(1998)
Bioorganic Chemistry: Peptides and Proteins
, pp. 27-64
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Hecht, S.M.1
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6
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29144515845
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note
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Reagent abbreviations used: HOAt = 7-aza-1-hydroxybenzotriazole; HOBt = N-hydroxybenzotriazole; PyAOP = 7-azobenzotriazolyoxytris(pyrrolidino) phosphonium hexafluorophosphate; PyBOP = 1-benzotriazolyoxytris(pyrrolidino) phosphonium hexafluorophosphate; N-HBTU = N-[(1H-benzotriazol-1-yl)- (dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate N-oxide; N-HATU = N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-yl-methylene]-N- methylmethanaminium hexafluorophosphate N-oxide.
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8
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33845312505
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L.A. Carpino, A. El-Faham, C.A. Minor, and F. Albericio J. Chem. Soc., Chem. Commun. 1994 201
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(1994)
J. Chem. Soc., Chem. Commun.
, pp. 201
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Carpino, L.A.1
El-Faham, A.2
Minor, C.A.3
Albericio, F.4
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9
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0002766774
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I. Abdelmoty, F. Albericio, L.A. Carpino, B.M. Foxman, and S. Kates Lett. Pept. Sci. 1 1994 57
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(1994)
Lett. Pept. Sci.
, vol.1
, pp. 57
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Abdelmoty, I.1
Albericio, F.2
Carpino, L.A.3
Foxman, B.M.4
Kates, S.5
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10
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0001304727
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L.A. Carpino, H. Imazumi, A. El-Faham, F.J. Ferrer, C. Zhang, Y. Lee, B.M. Foxman, P. Henklein, C. Hanay, C. Mügge, H. Wenschuh, J. Klose, M. Beyermann, and M. Bienert Angew. Chem., Int. Ed. 41 2002 442
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(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 442
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Carpino, L.A.1
Imazumi, H.2
El-Faham, A.3
Ferrer, F.J.4
Zhang, C.5
Lee, Y.6
Foxman, B.M.7
Henklein, P.8
Hanay, C.9
Mügge, C.10
Wenschuh, H.11
Klose, J.12
Beyermann, M.13
Bienert, M.14
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12
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29144493476
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I. Koppel, J. Kopple, I. Leito, V. Pihl, L. Grehn, and U. Ragnarsson J. Chem. Res., Synop. 1993 446
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(1993)
J. Chem. Res., Synop.
, pp. 446
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Koppel, I.1
Kopple, J.2
Leito, I.3
Pihl, V.4
Grehn, L.5
Ragnarsson, U.6
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13
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0034720920
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L.A. Carpino, H. Imazumi, B.M. Foxman, M.J. Vela, P. Henklein, A. El-Faham, J. Klose, and M. Bienert Org. Lett. 2 2000 2253
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(2000)
Org. Lett.
, vol.2
, pp. 2253
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Carpino, L.A.1
Imazumi, H.2
Foxman, B.M.3
Vela, M.J.4
Henklein, P.5
El-Faham, A.6
Klose, J.7
Bienert, M.8
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14
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29144528955
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note
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HOAt is commercially available ($2000/mol) or can be synthesized from 3-hydroxy-2-nitropyridine.
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21
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0034728203
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3Al promoted condensation of 2-pyridinethiol esters with amino esters has also been reported M. Kurosu Tetrahedron Lett. 41 2000 591
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(2000)
Tetrahedron Lett.
, vol.41
, pp. 591
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Kurosu, M.1
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24
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29144443711
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U.S. Patent 3,904,612, 1975.
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Nagasawa, T.; Kuroiwa, K.; Narita, K. U.S. Patent 3,904,612, 1975.
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Nagasawa, T.1
Kuroiwa, K.2
Narita, K.3
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25
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29144453840
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See Supporting Information of Ref. 13.
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See Supporting Information of Ref. 13.
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-
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26
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29144498376
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note
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4PS: C, 34.38; H, 4.98; N, 14.58. Found: C, 34.39; H, 5.12; N, 14.40.
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27
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29144461682
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note
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28-31.
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-
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28
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29144488456
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note
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Abbreviations used: Cbz = (benzy1oxy)carbonyl; Phe = (S)-phenylalanine; Val = (S)-valine; Ala = (S)-alanine; Gly = glycine; Phg = (S)-phenylglycine; Pro = (S)-proline; Aib = 2-aminoisobutyric acid.
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29
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29144489528
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note
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2.
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31
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29144515844
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note
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1H NMR peaks for active ester with reagent 14: 8.80 ppm, doublet, 7.27 ppm, triplet (aromatic protons); with 16: 6.99 ppm, singlet (aromatic proton) and 2.53 ppm (2 × Me).
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35
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0035914675
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F. Albericio, M.A. Bailen, R. Chinchilla, D.J. Dodsworth, and C. Najera Tetrahedron 57 2001 9607
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(2001)
Tetrahedron
, vol.57
, pp. 9607
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Albericio, F.1
Bailen, M.A.2
Chinchilla, R.3
Dodsworth, D.J.4
Najera, C.5
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36
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0028862474
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H. Wenschuh, M. Beyermann, H. Haber, J.K. Seydel, E. Krause, M. Bienert, L.A. Carpino, A. El-Faham, and F. Albericio J. Org. Chem. 60 1995 405
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(1995)
J. Org. Chem.
, vol.60
, pp. 405
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Wenschuh, H.1
Beyermann, M.2
Haber, H.3
Seydel, J.K.4
Krause, E.5
Bienert, M.6
Carpino, L.A.7
El-Faham, A.8
Albericio, F.9
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