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Volumn 34, Issue 6, 2004, Pages 1049-1056

An Improved Preparation of N2-tert-Butoxycarbonyl- and N 2-Benzyloxycarbonyl-(S)-2,4-diaminobutanoic Acids

Author keywords

Hofmann rearrangement; Iodosobenzene diacetate; Non proteinogenic amino acids; Protecting groups

Indexed keywords

2,4 DIAMINOBUTYRIC ACID; ACETIC ACID ETHYL ESTER; ACETOACETIC ACID DERIVATIVE; ACETONITRILE; AMINO ACID DERIVATIVE; ANTIBIOTIC AGENT; BENZENE DERIVATIVE; CARBONYL DERIVATIVE; DIOXANE; GLUTAMINE DERIVATIVE; IODOSOBENZENE DIACETATE; N 2 BENZYLOXYCARBONYL 2,4 DIAMINOBUTANOIC ACID; N 2 TERT BUTOXYCARBONYL 2,4 DIAMINOBUTANOIC ACID; N BENZYLOXYCARBONYLGLUTAMINE; N TERT BUTOXYCARBONYLGLUTAMINE; TETRAHYDROFURAN; UNCLASSIFIED DRUG; WATER;

EID: 1842533219     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120028636     Document Type: Article
Times cited : (10)

References (33)
  • 1
    • 1842476538 scopus 로고
    • Antibiotics and synthetic antibacterials
    • Foye, W.O., Ed.; Lea & Febiger: Philadelphia - London
    • Foye, W.O.; Perlman, D. Antibiotics and synthetic antibacterials. In Principles of Medicinal Chemistry, 3rd Ed.; Foye, W.O., Ed.; Lea & Febiger: Philadelphia - London, 1989; 679-716.
    • (1989) Principles of Medicinal Chemistry, 3rd Ed. , pp. 679-716
    • Foye, W.O.1    Perlman, D.2
  • 5
    • 0035662453 scopus 로고    scopus 로고
    • Acetyldiaminobutanoic acid, a potential lathyrogenic amino acid in leaves of Acacia angustissima
    • Reed, J.D.; Gebre-Mariam, G.; Robinson, C.J.; Hanson, J.; Odenyo, A.; Treichel, P.M. Acetyldiaminobutanoic acid, a potential lathyrogenic amino acid in leaves of Acacia angustissima. J. Sci. Food Agr. 2001, 81, 1481-1486.
    • (2001) J. Sci. Food Agr. , vol.81 , pp. 1481-1486
    • Reed, J.D.1    Gebre-Mariam, G.2    Robinson, C.J.3    Hanson, J.4    Odenyo, A.5    Treichel, P.M.6
  • 6
    • 0020446397 scopus 로고
    • Synthesis and pharmacological characterization in vitro cyclic enkephalin analogues: Effect of conformational constraints on opiate receptor selectivity
    • DiMaio, J.; Nguyen, T.M.; Lemieux, C.; Schiller, P.W. Synthesis and pharmacological characterization in vitro cyclic enkephalin analogues: effect of conformational constraints on opiate receptor selectivity. J. Med. Chem. 1982, 25, 1432-1438.
    • (1982) J. Med. Chem. , vol.25 , pp. 1432-1438
    • DiMaio, J.1    Nguyen, T.M.2    Lemieux, C.3    Schiller, P.W.4
  • 7
    • 0019837199 scopus 로고
    • γ-(4-azidophenylacetyl)-D-α, γ-diaminobutyric acid] insulin: Its preparation and properties
    • γ -(4-azidophenylacetyl)-D-α, γ-diaminobutyric acid] insulin: its preparation and properties. Z. Physiol. Chem. 1981, 362, 1237-1245.
    • (1981) Z. Physiol. Chem. , vol.362 , pp. 1237-1245
    • Saunders, D.J.1    Brandenburg, D.2
  • 8
    • 0028966767 scopus 로고
    • A new somatostatin analog with optimized ring size inhibits neointima formation induced by balloon injury in rats without altering growth hormone release
    • Thurieau, C.; Jankiak, P.; Krantic, S.; Guyard, C.; Pillon, A. A new somatostatin analog with optimized ring size inhibits neointima formation induced by balloon injury in rats without altering growth hormone release. Eur. J. Med. Chem. 1995, 30, 115-122.
    • (1995) Eur. J. Med. Chem. , vol.30 , pp. 115-122
    • Thurieau, C.1    Jankiak, P.2    Krantic, S.3    Guyard, C.4    Pillon, A.5
  • 9
    • 0035802994 scopus 로고    scopus 로고
    • Novel spermine amino acid conjugates and basic tripeptides enhance cleavage of the hairpin ribozyme at low magnesium ion concentration
    • Stolze, K.; Holmes, S.; Earnshaw, D.; Singh, M.; Stetsenko, D.; Williams, D.; Gait, M.J. Novel spermine amino acid conjugates and basic tripeptides enhance cleavage of the hairpin ribozyme at low magnesium ion concentration. Bioorg. Med. Chem. Lett. 2001, 11, 3007-3010.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 3007-3010
    • Stolze, K.1    Holmes, S.2    Earnshaw, D.3    Singh, M.4    Stetsenko, D.5    Williams, D.6    Gait, M.J.7
  • 10
    • 0034676308 scopus 로고    scopus 로고
    • Design and synthesis of pyrrolidine-5,5-trans-lactams (5-oxo-hexahydro-pyrrolo[3,2-b]pyrroles) as novel mechanism-based inhibitors of human cytomegalovirus protease. 1. The α-methyl-trans-lactam template
    • Borthwick, A.D.; Angier, S.J.; Crame, A.J.; Exall, A.M.; Haley, T.M.; Hart, G.J.; Mason, A.M.; Pennell, A.M.K.; Weingarten, G.G. Design and synthesis of pyrrolidine-5,5-trans-lactams (5-oxo-hexahydro-pyrrolo[3,2-b]pyrroles) as novel mechanism-based inhibitors of human cytomegalovirus protease. 1. The α-methyl-trans-lactam template. J. Med. Chem. 2000, 43, 4452-4464.
    • (2000) J. Med. Chem. , vol.43 , pp. 4452-4464
    • Borthwick, A.D.1    Angier, S.J.2    Crame, A.J.3    Exall, A.M.4    Haley, T.M.5    Hart, G.J.6    Mason, A.M.7    Pennell, A.M.K.8    Weingarten, G.G.9
  • 12
    • 0031044977 scopus 로고    scopus 로고
    • Analogues of N-α-(4-amino-4-deoxypteroyl)-N-δ -hemiphthaloyl-L-ornithine (PT523) modified in the side chain: Synthesis and biological evaluation
    • Rosowsky, A.; Vaidya, C.M.; Bader, H.; Wright, J.E.; Teicher, B.A. Analogues of N-α-(4-amino-4-deoxypteroyl)-N-δ -hemiphthaloyl-L-ornithine (PT523) modified in the side chain: synthesis and biological evaluation. J. Med. Chem. 1997, 40, 286-299.
    • (1997) J. Med. Chem. , vol.40 , pp. 286-299
    • Rosowsky, A.1    Vaidya, C.M.2    Bader, H.3    Wright, J.E.4    Teicher, B.A.5
  • 13
    • 0034850195 scopus 로고    scopus 로고
    • Synthesis and evaluation of dipeptide amides containing N-ω-nitroarginine and D-2,4-diaminobutyric acids as inhibitors of neuronal nitric oxide synthase
    • Huang, H.; Martasek, P.; Roman, L.J.; Silverman, R.B. Synthesis and evaluation of dipeptide amides containing N-ω-nitroarginine and D-2,4-diaminobutyric acids as inhibitors of neuronal nitric oxide synthase. J. Enzyme. Inhib. 2001, 16, 233-239.
    • (2001) J. Enzyme. Inhib. , vol.16 , pp. 233-239
    • Huang, H.1    Martasek, P.2    Roman, L.J.3    Silverman, R.B.4
  • 14
    • 0035951935 scopus 로고    scopus 로고
    • First synthesis of blastidic acid, a component amino acid in an antibiotic, blasticidin S
    • Nomoto, S.; Shimoyama, A. First synthesis of blastidic acid, a component amino acid in an antibiotic, blasticidin S. Tetrahedron Lett. 2001, 42, 1753-1755.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1753-1755
    • Nomoto, S.1    Shimoyama, A.2
  • 15
    • 1842424049 scopus 로고    scopus 로고
    • Gene delivery/transfection composition comprising poly(2, 4-diaminobutyric acid) (PDBA) and recombinant virus vector. PCT Int. Appl. WO 01 29,244. CA 134: 291092t
    • Goto, T.; Iijima, Y.; Shimada, T. Gene delivery/transfection composition comprising poly(2,4-diaminobutyric acid) (PDBA) and recombinant virus vector. PCT Int. Appl. WO 01 29,244. CA 134: 291092t.
    • Goto, T.1    Iijima, Y.2    Shimada, T.3
  • 16
    • 0034479087 scopus 로고    scopus 로고
    • Antitumour effect of L-2,4 diaminobutyric acid on a hepatoma cell line
    • Blind, P.J.; Waldenstrom, A.; Berggren, D.; Ronquist, G. Antitumour effect of L-2,4 diaminobutyric acid on a hepatoma cell line. Anticancer Res. 2000, 20, 4275-4278.
    • (2000) Anticancer Res. , vol.20 , pp. 4275-4278
    • Blind, P.J.1    Waldenstrom, A.2    Berggren, D.3    Ronquist, G.4
  • 18
    • 0023848008 scopus 로고
    • The cytolytic effect of L-2,4-diaminobutyric acid with malignant glioma cells and fibroblasts
    • Panasci, L.; McQuillan, A.; Feindel, W. The cytolytic effect of L-2,4-diaminobutyric acid with malignant glioma cells and fibroblasts. Cancer Chemoth. Pharm. 1988, 21, 143-144.
    • (1988) Cancer Chemoth. Pharm. , vol.21 , pp. 143-144
    • Panasci, L.1    McQuillan, A.2    Feindel, W.3
  • 19
    • 0030990857 scopus 로고    scopus 로고
    • The new α-amino acid N-ω-hydroxy-nor-L-arginine: A high-affinity inhibitor of arginase well adapted to bind to its manganese cluster
    • Custot, J.; Moali, C.; Brollo, M.; Boucher, J.L.; Delaforge, M.; Mansuy, D.; Tenu, J.P.; Zimmermann, J.L. The new α-amino acid N-ω -hydroxy-nor-L-arginine: a high-affinity inhibitor of arginase well adapted to bind to its manganese cluster. J. Am. Chem. Soc. 1997, 119, 4086-4087.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 4086-4087
    • Custot, J.1    Moali, C.2    Brollo, M.3    Boucher, J.L.4    Delaforge, M.5    Mansuy, D.6    Tenu, J.P.7    Zimmermann, J.L.8
  • 20
    • 0000754393 scopus 로고
    • Synthesis of peptides containing unnatural, metal ligating residues: Aminodiacetic acid as a peptide side chain
    • Ruan, F.; Chen, Y.; Itoh, K.; Sasaki, T.; Hopkins, P.B. Synthesis of peptides containing unnatural, metal ligating residues: aminodiacetic acid as a peptide side chain. J. Org. Chem. 1991, 56, 4347-4354.
    • (1991) J. Org. Chem. , vol.56 , pp. 4347-4354
    • Ruan, F.1    Chen, Y.2    Itoh, K.3    Sasaki, T.4    Hopkins, P.B.5
  • 21
    • 0033048817 scopus 로고    scopus 로고
    • Synthesis and study of peptides with semirigid i and i + 7 side-chain bridges designed for alpha-helix stabilization
    • Yu, C.X.; Taylor, J.W. Synthesis and study of peptides with semirigid i and i + 7 side-chain bridges designed for alpha-helix stabilization. Bioorg. Med. Chem. 1999, 7, 161-175.
    • (1999) Bioorg. Med. Chem. , vol.7 , pp. 161-175
    • Yu, C.X.1    Taylor, J.W.2
  • 22
    • 0027208734 scopus 로고
    • Metal chelating amino acids in the design of peptides and proteins. Synthesis of Nα-Fmoc/but protected amino acids incorporating aminodiacetic acid moiety
    • Kazimierski, W.M. Metal chelating amino acids in the design of peptides and proteins. Synthesis of Nα-Fmoc/But protected amino acids incorporating aminodiacetic acid moiety. Tetrahedron Lett. 1993, 34, 4493.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 4493
    • Kazimierski, W.M.1
  • 24
    • 0035536578 scopus 로고    scopus 로고
    • 2-benzyl-oxycarbonyl-(S)-2-amino-3-(dimethylamino)propanoic acid
    • 2-benzyl-oxycarbonyl-(S)-2-amino-3-(dimethylamino)propanoic acid. Org. Prep. Proc. Int. 2001, 33, 379-381.
    • (2001) Org. Prep. Proc. Int. , vol.33 , pp. 379-381
    • Andruszkiewicz, R.1    Walkowiak, A.2
  • 25
    • 0036456194 scopus 로고    scopus 로고
    • Efficient synthesis of N-benzyloxycarbonyl and N-tert-butoxycarbonyl-(S)-isoserine and their derivatives
    • Andruszkiewicz, R.; Wyszogrodzka, M. Efficient synthesis of N-benzyloxycarbonyl and N-tert-butoxycarbonyl-(S)-isoserine and their derivatives. Synlett 2002, 2101-2103.
    • (2002) Synlett , pp. 2101-2103
    • Andruszkiewicz, R.1    Wyszogrodzka, M.2
  • 26
    • 0037733045 scopus 로고    scopus 로고
    • Synthesis of orthogonally protected (3R,4S)-and (3S,4S)-4,5-diamino-3-hydroxypentanoic acids
    • Czajgucki, Z.; Sowiński, P.; Andruszkiewicz, R. Synthesis of orthogonally protected (3R,4S)-and (3S,4S)-4,5-diamino-3-hydroxypentanoic acids. Amino Acids 2003, 24, 289-291.
    • (2003) Amino Acids , vol.24 , pp. 289-291
    • Czajgucki, Z.1    Sowiński, P.2    Andruszkiewicz, R.3
  • 28
    • 0242684600 scopus 로고    scopus 로고
    • Structure-activity relationships for a series of peptidomimetic antimicrobial prodrugs containing glutamine analogues
    • Marshall, N.J.; Andruszkiewicz, R.; Gupta, S.; Milewski, S.; Payne, J.W. Structure-activity relationships for a series of peptidomimetic antimicrobial prodrugs containing glutamine analogues. J. Antimicrob. Chemoth. 2003, 51, 821-831.
    • (2003) J. Antimicrob. Chemoth. , vol.51 , pp. 821-831
    • Marshall, N.J.1    Andruszkiewicz, R.2    Gupta, S.3    Milewski, S.4    Payne, J.W.5
  • 29
    • 0001163026 scopus 로고    scopus 로고
    • α-protected L-asparagines with iodobenzene diacetate. A practical route to β-amino-L-alanine derivatives
    • α-protected L-asparagines with iodobenzene diacetate. A practical route to β-amino-L-alanine derivatives. J. Org. Chem. 1997, 62, 6918-6920.
    • (1997) J. Org. Chem. , vol.62 , pp. 6918-6920
    • Zhang, L.H.1    Kauffman, G.S.2    Pesti, J.A.3    Yin, J.4
  • 30
    • 33947488731 scopus 로고
    • Studies on polypeptides. XXX. Synthetic peptides related to the N-terminus of bovine pancreatic ribonuclease (positions 8-13)
    • Hofmann, K.; Haas, W.; Smithers, M.J.; Wells, R.D.; Wolman, Y.; Yanaihara, N.; Zanetti, G. Studies on polypeptides. XXX. Synthetic peptides related to the N-terminus of bovine pancreatic ribonuclease (positions 8-13). J. Am. Chem. Soc. 1965, 87, 620-631.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 620-631
    • Hofmann, K.1    Haas, W.2    Smithers, M.J.3    Wells, R.D.4    Wolman, Y.5    Yanaihara, N.6    Zanetti, G.7
  • 31
    • 0015234266 scopus 로고
    • Studies on polypeptides. XLIX. Fragment condensation with peptide derivatives related to the primary structure of ribonuclease T
    • Beacham, J.; Dupuis, G.; Finn, F.M.; Storey, H.T.; Yanaihara, C.; Yanaihara, N.; Hofmann, K. Studies on polypeptides. XLIX. Fragment condensation with peptide derivatives related to the primary structure of ribonuclease T. J. Am. Chem. Soc. 1971, 93, 5526-5539.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 5526-5539
    • Beacham, J.1    Dupuis, G.2    Finn, F.M.3    Storey, H.T.4    Yanaihara, C.5    Yanaihara, N.6    Hofmann, K.7
  • 32
    • 1842332471 scopus 로고
    • Amino acids and peptides. CXXXV. Synthesis of derivatives and peptides of α-amino-β-guanidinopropionic acid and α-amino-γ -guanidinobutyric acid
    • Brtnik, F.; Zaoral, M. Amino acids and peptides. CXXXV. Synthesis of derivatives and peptides of α-amino-β-guanidinopropionic acid and α-amino-γ-guanidinobutyric acid. Collect. Czech. Chem. Commun. 1976, 41, 2969-2977.
    • (1976) Collect. Czech. Chem. Commun. , vol.41 , pp. 2969-2977
    • Brtnik, F.1    Zaoral, M.2
  • 33
    • 0014712820 scopus 로고
    • Peptide XIII. Synthese eines cyclischen decapeptids mit der für das circulin B angegebenen structur
    • Arold, H. Peptide XIII. Synthese eines cyclischen decapeptids mit der für das circulin B angegebenen structur. Justus Liebig's Ann. Chem. 1970, 731, 152-160.
    • (1970) Justus Liebig's Ann. Chem. , vol.731 , pp. 152-160
    • Arold, H.1


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