-
1
-
-
0029014960
-
-
For instance, N-methylamino acids are important constituents of the therapeutically promising class of N-methylated peptides. Recent example: Schmidt, R.; Kalman, A.; Chung, N. N.; Lemieux, C.; Horvath, C.; Schiller, P. W. Int. J. Pept. Protein Res. 1995, 46, 47.
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Schmidt, R.1
Kalman, A.2
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Lemieux, C.4
Horvath, C.5
Schiller, P.W.6
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2
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7044263277
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For reviews, see: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (b) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288.
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Thompson, L.A.1
Ellman, J.A.2
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3
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0030477258
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For reviews, see: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (b) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288.
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Balkenhohl, F.1
Von Dem Bussche-Hünnefeld, C.2
Lansky, A.3
Zechel, C.4
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4
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0028833961
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-
For selected examples, see: (a) Gordon, D. W.; Steele, J. Bioorg. Med. Chem. Lett. 1995, 5, 47. (b) Matthews, J.; Rivero, R. A. J. Org. Chem. 1997, 62, 6090. (c) Bilodeau, M. T.; Cunningham, A. M. J. Org. Chem. 1998, 63, 2800. (d) Matthews, J.; Rivero, R. A. J. Org. Chem. 1998, 63, 4808.
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Bioorg. Med. Chem. Lett.
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, pp. 47
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Gordon, D.W.1
Steele, J.2
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5
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0030876296
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For selected examples, see: (a) Gordon, D. W.; Steele, J. Bioorg. Med. Chem. Lett. 1995, 5, 47. (b) Matthews, J.; Rivero, R. A. J. Org. Chem. 1997, 62, 6090. (c) Bilodeau, M. T.; Cunningham, A. M. J. Org. Chem. 1998, 63, 2800. (d) Matthews, J.; Rivero, R. A. J. Org. Chem. 1998, 63, 4808.
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J. Org. Chem.
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Matthews, J.1
Rivero, R.A.2
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6
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0028833961
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-
For selected examples, see: (a) Gordon, D. W.; Steele, J. Bioorg. Med. Chem. Lett. 1995, 5, 47. (b) Matthews, J.; Rivero, R. A. J. Org. Chem. 1997, 62, 6090. (c) Bilodeau, M. T.; Cunningham, A. M. J. Org. Chem. 1998, 63, 2800. (d) Matthews, J.; Rivero, R. A. J. Org. Chem. 1998, 63, 4808.
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J. Org. Chem.
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Bilodeau, M.T.1
Cunningham, A.M.2
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7
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0032504083
-
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For selected examples, see: (a) Gordon, D. W.; Steele, J. Bioorg. Med. Chem. Lett. 1995, 5, 47. (b) Matthews, J.; Rivero, R. A. J. Org. Chem. 1997, 62, 6090. (c) Bilodeau, M. T.; Cunningham, A. M. J. Org. Chem. 1998, 63, 2800. (d) Matthews, J.; Rivero, R. A. J. Org. Chem. 1998, 63, 4808.
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Matthews, J.1
Rivero, R.A.2
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8
-
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0345401075
-
-
note
-
5b of sulfonamide derivatives. The scope of these methods, however, was not demonstrated beyond N-methylation.
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14
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0025916460
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(d) Bonnat, M.; Hercouet, A.; Le Corre, M. Synth. Commun. 1991, 21, 1579.
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Synth. Commun.
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Bonnat, M.1
Hercouet, A.2
Le Corre, M.3
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15
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0017296453
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(a) Roeske, R. W.; Weitl, F. L.; Prasad, K. U.; Thompson, R. M. J. Org. Chem. 1976, 41, 1260.
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Roeske, R.W.1
Weitl, F.L.2
Prasad, K.U.3
Thompson, R.M.4
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17
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0025819848
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(c) Chu, K. S.; Negrete, G. R.; Konopelski, J. P. J. Org. Chem. 1991, 56, 5196.
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Chu, K.S.1
Negrete, G.R.2
Konopelski, J.P.3
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18
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0003068388
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Maia, H. L. S., Ed.; ESCOM: Leiden
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(d) Cuervo, J. H.; Weitl, F.; Ostresh, J. M.; Hamashin, V. T.; Hannah, A. L.; Houghten, R. A. In Peptides 1994, Proceedings of the 23rd European Peptide Symposium; Maia, H. L. S., Ed.; ESCOM: Leiden, 1995; p 465.
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Peptides 1994, Proceedings of the 23rd European Peptide Symposium
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Cuervo, J.H.1
Weitl, F.2
Ostresh, J.M.3
Hamashin, V.T.4
Hannah, A.L.5
Houghten, R.A.6
-
19
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0031562077
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For an example of a solid-phase synthesis of triamines from peptides on Merrifield resin, see: Nefzi, A.; Ostresh, J. M.; Meyer, J.-P.; Houghten, R. A. Tetrahedron Lett. 1997, 38, 931. Therein, acidic cleavage of borane-amine adducts is carried out with 1 M HCl/MeOH (65°C, >12 h). Also, with this support, product cleavage with HF requires special equipment.
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Tetrahedron Lett.
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, pp. 931
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Nefzi, A.1
Ostresh, J.M.2
Meyer, J.-P.3
Houghten, R.A.4
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22
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33947334381
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(c) Young, D. E.; McAchran, G. E.; Shore, S. G. J. Am. Chem. Soc. 1966, 88, 4390.
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Young, D.E.1
McAchran, G.E.2
Shore, S.G.3
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23
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0030570917
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-
For examples of amide reductions, see: (a) Paikoff, S. J.; Wilson, T. E.; Cho, C. Y.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5653. (b) Brown, P. J.; Hurley, K. P.; Stuart, L. W.; Willson, T. M. Synthesis 1997, 778.
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Tetrahedron Lett.
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, pp. 5653
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Paikoff, S.J.1
Wilson, T.E.2
Cho, C.Y.3
Schultz, P.G.4
-
24
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0030808173
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For examples of amide reductions, see: (a) Paikoff, S. J.; Wilson, T. E.; Cho, C. Y.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5653. (b) Brown, P. J.; Hurley, K. P.; Stuart, L. W.; Willson, T. M. Synthesis 1997, 778.
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Synthesis
, pp. 778
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Brown, P.J.1
Hurley, K.P.2
Stuart, L.W.3
Willson, T.M.4
-
25
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0031767227
-
-
For a recent example of peptide reduction/piperidine treatment on methylbenzhydrylamine polystyrene resin followed by HF cleavage, see: Ostresh, J. M.; Schoner, C. C.; Hamashin, V. T.; Nefzi, A.; Meyer, J.-P.; Houghten, R. A. J. Org. Chem. 1998, 63, 8622.
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Ostresh, J.M.1
Schoner, C.C.2
Hamashin, V.T.3
Nefzi, A.4
Meyer, J.-P.5
Houghten, R.A.6
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28
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84952239926
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(b) Hutchins, R. O.; Learn, K.; Nazer, B.; Pytlewski, D. Org. Prep. Proc. Int. 1984, 16, 335.
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Org. Prep. Proc. Int.
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Hutchins, R.O.1
Learn, K.2
Nazer, B.3
Pytlewski, D.4
-
31
-
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0344107182
-
-
note
-
It was found that the reduction of unhindered N-acylamino acids such as 1a is accompanied by significant loss of material from the resin, presumably through reductive cleavage of the ester-based linker (ref 16) if more then 3 equiv of diborane is employed.
-
-
-
-
32
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0000851591
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Kornet, M. J.; Thio, P. A.; Tan, S. I. J. Org. Chem. 1968, 33, 3637.
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J. Org. Chem.
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Kornet, M.J.1
Thio, P.A.2
Tan, S.I.3
-
33
-
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0344969680
-
-
note
-
2 and dried under high vacuum for >12 h.
-
-
-
-
34
-
-
0344969678
-
-
note
-
Beads bearing the resulting borane-amine complex give a negative on the BPB test (yellow-green beads). A strong positive result (dark blue beads) is obtained following oxidative workup and neutralizing washes of the resin-bound secondary amine.
-
-
-
-
35
-
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0344969679
-
-
note
-
20 Column: Zorbax SB-C18 (4.6 × 150 mm, 5 mm). Eluent: linear gradient of 60-20% 0.1% aqueous TFA/acetonitrile over 20 min. Flow rate: 1 mL/ min. Analysis: UV diode-array detection, 190-400 nm.
-
-
-
-
36
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0000533290
-
-
Einarsson, S.; Josefsson, B.; Lagerkvist, S. J. Chromatogr. 1983, 282, 609.
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Einarsson, S.1
Josefsson, B.2
Lagerkvist, S.3
-
37
-
-
0344538720
-
-
note
-
Conditions similar to those of ref 19 except for the eluent: 60-10% over 50 min.
-
-
-
-
38
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0007680883
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Saegusa, T.; Kobayashi, S.; Ishiguro, M. Macromolecules 1974, 7, 958.
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Macromolecules
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Saegusa, T.1
Kobayashi, S.2
Ishiguro, M.3
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