SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 3, 2009, Pages 407-410

One-pot synthesis of ureido peptides and urea-tethered glycosylated amino acids employing deoxo-fluor and TMSN3

(4) Hemantha, H P a Chennakrishnareddy, G a Vishwanatha, T M a Sureshbabu, V V a

a BANGALORE UNIVERSITY (India)

Author keywords

Acyl fluoride; Deoxo fluor; Neoglycopeptides; Peptidomimetics; Ureido linkage

Indexed keywords

EID: 62249137102 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087538 Document Type: Article

Times cited : (30)

References (36)

1
- 33748226252
- Liskamp, R. M. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 633.
- (1994) Angew. Chem., Int. Ed. Engl , vol.33 , pp. 633
- Liskamp, R.M.J.¹

2
- 0542421525
- Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
- (1998) Acc. Chem. Res , vol.31 , pp. 173
- Gellman, S.H.¹

3
- 0000517240
- Burgess, K.; Linthicum, D. S.; Shin, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 907.
- (1995) Angew. Chem., Int. Ed. Engl , vol.34 , pp. 907
- Burgess, K.¹ Linthicum, D.S.² Shin, H.³

4
- 0002037724
- Nowick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith, E. M.; Ziller, J. M. J. Am. Chem. Soc. 1995, 117, 89.
- (1995) J. Am. Chem. Soc , vol.117 , pp. 89
- Nowick, J.S.¹ Abdi, M.² Bellamo, K.A.³ Love, J.A.⁴ Martinez, E.J.⁵ Noronha, G.⁶ Smith, E.M.⁷ Ziller, J.M.⁸

5
- 0032911804
- Nowick, J. S. Acc. Chem. Res. 1999, 32, 287.
- (1999) Acc. Chem. Res , vol.32 , pp. 287
- Nowick, J.S.¹

6
- 62249146653
- Fischer, L.; Semetey, V.; Lozano, J. M.; Schaffiner, A. P.; Briand, J. P.; Didierjean, C.; Guichard, G. Eur. J. Org. Chem. 2007, 3944.
- (2007) Eur. J. Org. Chem , pp. 3944
- Fischer, L.¹ Semetey, V.² Lozano, J.M.³ Schaffiner, A.P.⁴ Briand, J.P.⁵ Didierjean, C.⁶ Guichard, G.⁷

7
- 0141789882
- Patil, B. S.; Vasanthakumar, G. R.; Sureshbabu, V. V. J. Org. Chem. 2003, 68, 7274.
- (2003) J. Org. Chem , vol.68 , pp. 7274
- Patil, B.S.¹ Vasanthakumar, G.R.² Sureshbabu, V.V.³

8
- 0032831145
- Boeijen, A.; Liskamp, R. M. J. Eur. J. Org. Chem. 1999, 2127.
- (1999) Eur. J. Org. Chem , pp. 2127
- Boeijen, A.¹ Liskamp, R.M.J.²

9
- 0033599370
- Tamilarasu, N.; Huq, F.; Rana, T. M. J. Am. Chem. Soc. 1999, 121, 1579.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 1579
- Tamilarasu, N.¹ Huq, F.² Rana, T.M.³

10
- 10644262165
- Bakshi, P.; Wolfe, M. S. J. Med. Chem. 2004, 47, 6485.
- (2004) J. Med. Chem , vol.47 , pp. 6485
- Bakshi, P.¹ Wolfe, M.S.²

11
- 0001005576
- Nowick, J. S.; Holmer, D. L.; Noronha, G.; Smith, E. M.; Nguyen, J. M.; Huang, S. L. J. Org. Chem. 1996, 61, 3929.
- (1996) J. Org. Chem , vol.61 , pp. 3929
- Nowick, J.S.¹ Holmer, D.L.² Noronha, G.³ Smith, E.M.⁴ Nguyen, J.M.⁵ Huang, S.L.⁶

12
- 0035861714
- Boeijen, A.; Ameijde, J. v.; Liskamp, R. M. J. J. Org. Chem. 2001, 6, 8454.
- (2001) J. Org. Chem , vol.6 , pp. 8454
- Boeijen, A.¹ Ameijde, J.V.² Liskamp, R.M.J.³

13
- 0033550306
- Guichard, G.; Semetey, V.; Didierjean, C.; Aubry, A.; Briand, J. P.; Rodriguez, M. J. Org. Chem. 1999, 64, 8702.
- (1999) J. Org. Chem , vol.64 , pp. 8702
- Guichard, G.¹ Semetey, V.² Didierjean, C.³ Aubry, A.⁴ Briand, J.P.⁵ Rodriguez, M.⁶

14
- 4544248532
- Myers, A. C.; Kowalski, J. A.; Lipton, M. A. Bioorg. Med. Chem. Lett. 2004, 14, 5219.
- (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 5219
- Myers, A.C.¹ Kowalski, J.A.² Lipton, M.A.³

15
- 33749119341
- Sureshbabu, V. V.; Patil, B. S.; Venkataramanarao, R. J. Org. Chem. 2006, 71, 7697.
- (2006) J. Org. Chem , vol.71 , pp. 7697
- Sureshbabu, V.V.¹ Patil, B.S.² Venkataramanarao, R.³

16
- 40049087671
- Sureshbabu, V. V.; Venkataramanarao, R.; Hemantha, H. P. Int. J. Pept. Res. Ther. 2008, 14, 34.
- (2008) Int. J. Pept. Res. Ther , vol.14 , pp. 34
- Sureshbabu, V.V.¹ Venkataramanarao, R.² Hemantha, H.P.³

17
- 27644594248
- Sureshbabu, V. V.; Kantharaju; Tantry, S. J. Int. J. Pept. Res. Ther. 2005, 11, 131.
- (2005) Int. J. Pept. Res. Ther , vol.11 , pp. 131
- Sureshbabu, V.V.¹ Kantharaju² Tantry, S.J.³

18
- 38349112611
- Sureshbabu, V. V.; Chennakrishnareddy, G.; Narendra, N. Tetrahedron Lett. 2008, 49, 1408.
- (2008) Tetrahedron Lett , vol.49 , pp. 1408
- Sureshbabu, V.V.¹ Chennakrishnareddy, G.² Narendra, N.³

19
- 42349114723
- Baumann, M.; Baxendale, I. R.; Ley, S. V.; Nikbin, N.; Smith, C. D.; Tierney, J. P. Org. Biomol. Chem. 2008, 6, 1577.
- (2008) Org. Biomol. Chem , vol.6 , pp. 1577
- Baumann, M.¹ Baxendale, I.R.² Ley, S.V.³ Nikbin, N.⁴ Smith, C.D.⁵ Tierney, J.P.⁶

20
- 0344507270
- (a) Lal, G. S.; Pez, G. P.; Pesaresi, R. J.; Prozonic, F. M. Chem. Commun. 1999, 215.
- (1999) Chem. Commun , pp. 215
- Lal, G.S.¹ Pez, G.P.² Pesaresi, R.J.³ Prozonic, F.M.⁴

21
- 0033578943
- (b) Lal, G. S.; Pez, G. P.; Pesaresi, R. J.; Prozonic, F. M.; Cheng, H. J. Org. Chem. 1999, 64, 7048.
- (1999) J. Org. Chem , vol.64 , pp. 7048
- Lal, G.S.¹ Pez, G.P.² Pesaresi, R.J.³ Prozonic, F.M.⁴ Cheng, H.⁵

22
- 0036456479
- Singh, R. P.; Shreeve, J. M. Synthesis 2002, 2561.
- (2002) Synthesis , pp. 2561
- Singh, R.P.¹ Shreeve, J.M.²

23
- 0034809281
- Singh, R. P.; Chakraborty, D.; Shreeve, J. M. J. Fluorine Chem. 2002, 111, 153.
- (2002) J. Fluorine Chem , vol.111 , pp. 153
- Singh, R.P.¹ Chakraborty, D.² Shreeve, J.M.³

24
- 37649021196
- Kangani, C. O.; Day, B. W.; Kelley, D. E. Tetrahedron Lett. 2008, 49, 914.
- (2008) Tetrahedron Lett , vol.49 , pp. 914
- Kangani, C.O.¹ Day, B.W.² Kelley, D.E.³

25
- 34447635856
- (a) Kangani, C. O.; Day, B. W.; Kelley, D. E. Tetrahedron Lett. 2007, 48, 5933.
- (2007) Tetrahedron Lett , vol.48 , pp. 5933
- Kangani, C.O.¹ Day, B.W.² Kelley, D.E.³

26
- 27944466810
- (b) Kangani, C. O.; Kelley, D. E. Tetrahedron Lett. 2005, 46, 8917.
- (2005) Tetrahedron Lett , vol.46 , pp. 8917
- Kangani, C.O.¹ Kelley, D.E.²

27
- 0034649742
- Tunoori, A. R.; White, J. M.; Georg, G. I. Org Lett. 2000, 2, 4091.
- (2000) Org Lett , vol.2 , pp. 4091
- Tunoori, A.R.¹ White, J.M.² Georg, G.I.³

28
- 0001475687
- Carpino, L. A.; Mansour, E. M. E.; El-Fahan, A. J. Org. Chem. 1993, 58, 4162.
- (1993) J. Org. Chem , vol.58 , pp. 4162
- Carpino, L.A.¹ Mansour, E.M.E.² El-Fahan, A.³

29
- 33846323284
- Kaduk, C.; Wenschuh, H.; Beyermann, M.; Forner, K.; Carpino, L. A.; Bienert, M. Lett. Pept. Sci. 1995, 2, 285.
- (1995) Lett. Pept. Sci , vol.2 , pp. 285
- Kaduk, C.¹ Wenschuh, H.² Beyermann, M.³ Forner, K.⁴ Carpino, L.A.⁵ Bienert, M.⁶

30
- 0035083123
- Utility of commercial activated zinc dust to deprotonate amine hydrochloride salts is documented. Sureshbabu et al. demonstrated the conversion of amino acid/peptide acid ester hydrochloride salts into the corresponding free amines, see: (a) Sureshbabu, V. V.; Ananda, K. J. Pept. Res. 2001, 57, 223.
- Utility of commercial activated zinc dust to deprotonate amine hydrochloride salts is documented. Sureshbabu et al. demonstrated the conversion of amino acid/peptide acid ester hydrochloride salts into the corresponding free amines, see: (a) Sureshbabu, V. V.; Ananda, K. J. Pept. Res. 2001, 57, 223.

31
- 0032564614
- For the use of zinc dust as HCl scavenger in peptide synthesis via N-Fmoc amino acid chlorides under non-Schotten-Baumann conditions, see: Gopi, H. N.; Sureshbabu, V. V. Tetrahedron Lett. 1998, 39, 9769.
- (b) For the use of zinc dust as HCl scavenger in peptide synthesis via N-Fmoc amino acid chlorides under non-Schotten-Baumann conditions, see: Gopi, H. N.; Sureshbabu, V. V. Tetrahedron Lett. 1998, 39, 9769.

32
- 0033980637
- For a similar application in N-Boc-Z-Fmoc amino acid fluoride couplings under neutral conditions, see: Sureshbabu, V. V.; Ananda, K. Lett. Pept. Sci. 2000, 7, 41.
- (c) For a similar application in N-Boc-Z-Fmoc amino acid fluoride couplings under neutral conditions, see: Sureshbabu, V. V.; Ananda, K. Lett. Pept. Sci. 2000, 7, 41.

33
- 0009453990
- For the preparation of oligomer-free Z-amino acids employing ZCl/Zn dust, see: Gopi, H. N.; Ananda, K.; Sureshbabu, V. V. Protein Pept. Lett. 1999, 6, 233.
- (d) For the preparation of oligomer-free Z-amino acids employing ZCl/Zn dust, see: Gopi, H. N.; Ananda, K.; Sureshbabu, V. V. Protein Pept. Lett. 1999, 6, 233.

34
- 62249154492
- 2O to afford the urea as a colorless crystalline solid.
- 2O to afford the urea as a colorless crystalline solid.

35
- 62249128584
- Selected Spectroscopic Data Fmoc-Val-ψ(NH-CO-NH)-Leu-OBzl (2b, white solid, mp 184°C. 1H NMR (300 MHz, DMSO, δ, 0.92 (12 H, m, 1.32-1.85 (4 H, m, 3.10 (2 H, s, 3.70-3.80 (2 H, m, 4.20 (1 H, t, 4.42 (2 H, m, 5.10 (1 H, d, 6.60-6.70 (2 H, m, 7.20-7.85 (13 H, m, 13C NMR (200 MHz, DMSO, δ, 18.5, 19.5, 22.0, 23.1, 24.5, 29.2, 40.3, 47.2, 59.0, 66.6, 120.0, 125.1, 126.5, 127.0, 127.2, 128.4, 129.3, 137.6, 141.2, 144.0, 155.4, 156.8, 176.4. HRMS: m/z calcd for C33H39N3NaO5: 580.2787; found: 580.2774 [M, Na, Z-Gly-ψ(NH-CO-NH)-Val-OMe (2d, Off-white solid, mp 159°C. 1H NMR (300 MHz, DMSO, δ, 0.93 (6 H, d, 3.14 (1 H, m, 3.58 (3 H, s, 4.51 (3 H, m, 5.30 (2 H, s, 6.10 (2 H, m, 6.48 (1 H, t, 7.20-7.40 (3 H, m, 13C NMR 200 MHz, DMSO, δ, 17.1, 31.1, 52.1, 56.2, 57.8, 65.4, 127.1, 127.2, 128.5, 141.2, 156.8, 157
- 8: 473.1900; found: 473.1918 [M + Na].

36
- 62249144006
- 4 buffer were added and the reaction mixture was warmed to 35°C. Sodium chlorite and bleach were added, and the reaction mixture was stirred till completion of reaction. A simple workup lead to the isolation of the desired sugar-6-acid. See: Jhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64, 2564.
- 4 buffer were added and the reaction mixture was warmed to 35°C. Sodium chlorite and bleach were added, and the reaction mixture was stirred till completion of reaction. A simple workup lead to the isolation of the desired sugar-6-acid. See: Jhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64, 2564.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.