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Volumn 9, Issue 5, 2003, Pages 312-319

Efficient protocols for the synthesis of enantiopure γ-amino acids with proteinogenic side chains

Author keywords

amino acids; Amino alcohols; Amino aldehydes; Enantiopurity; Wittig reaction

Indexed keywords

ACETIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; ALPHA AMINO ACID; AMIDE; AMINO ACID DERIVATIVE; AMINOALCOHOL; BENZYL ACETATE; ESTER DERIVATIVE; PEPTIDE DERIVATIVE;

EID: 0037603385     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/psc.458     Document Type: Article
Times cited : (26)

References (28)
  • 2
    • 33745502124 scopus 로고
    • Peptide mimetics for receptor ligands: Discovery, development, and medicinal perspectives
    • Giannis A, Kolter T. Peptide mimetics for receptor ligands: discovery, development, and medicinal perspectives. Angew. Chem., Int. Ed. Engl. 1993; 32: 1244-1267.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 1244-1267
    • Giannis, A.1    Kolter, T.2
  • 3
    • 0028355337 scopus 로고
    • Recent developments in the stereoselective synthesis of α-amino acids
    • Duthaler RO. Recent developments in the stereoselective synthesis of α-amino acids. Tetrahedron 1994; 50: 1539-1650.
    • (1994) Tetrahedron , vol.50 , pp. 1539-1650
    • Duthaler, R.O.1
  • 4
    • 8344249465 scopus 로고    scopus 로고
    • Enantiospecific synthesis of heterocycles from α-amino acids
    • Sardina FJ, Rapoport H. Enantiospecific synthesis of heterocycles from α-amino acids. Chem. Rev. 1996; 96: 1825-1872.
    • (1996) Chem. Rev. , vol.96 , pp. 1825-1872
    • Sardina, F.J.1    Rapoport, H.2
  • 5
    • 0029857593 scopus 로고    scopus 로고
    • Synthesis of medicinally useful lipidic α-amino acids, 2-amino alcohols and diamines
    • Kokotos G, Martin V, Constantinou-Kokotou V, Gibbons WA. Synthesis of medicinally useful lipidic α-amino acids, 2-amino alcohols and diamines. Amino Acids 1996; 11: 329-343.
    • (1996) Amino Acids , vol.11 , pp. 329-343
    • Kokotos, G.1    Martin, V.2    Constantinou-Kokotou, V.3    Gibbons, W.A.4
  • 6
    • 0030768259 scopus 로고    scopus 로고
    • Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics
    • Hanessian S, McNughton-Smith G, Lombart HG, Lubell WD. Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics. Tetrahedron 1997; 53: 12789-12854.
    • (1997) Tetrahedron , vol.53 , pp. 12789-12854
    • Hanessian, S.1    McNughton-Smith, G.2    Lombart, H.G.3    Lubell, W.D.4
  • 7
    • 0036903834 scopus 로고    scopus 로고
    • Combining chemical and biological techniques to produce modified proteins
    • Goody RS, Alexandrov K, Engelhard M. Combining chemical and biological techniques to produce modified proteins. ChemBioChem 2002; 3: 399-403.
    • (2002) ChemBioChem. , vol.3 , pp. 399-403
    • Goody, R.S.1    Alexandrov, K.2    Engelhard, M.3
  • 9
    • 0036397712 scopus 로고    scopus 로고
    • 3-nonapeptides folding to (P -helices with alternative twelve- and ten-membered hydrogen-bonded rings
    • 3-nonapeptides folding to (P -helices with alternative twelve- and ten-membered hydrogen-bonded rings. Helv. Chim. Acta 2002; 85: 2577-2593.
    • (2002) Helv. Chim. Acta , vol.85 , pp. 2577-2593
    • Rueping, M.1    Schreiber, J.V.2    Lelais, G.3    Jaun, B.4    Seebach, D.5
  • 10
    • 0035471135 scopus 로고    scopus 로고
    • β-Peptides: From structure to function
    • Cheng RP, Gellman SH, DeGrado WF. β-Peptides: From structure to function. Chem. Rev. 2001; 101: 3219-3232.
    • (2001) Chem. Rev. , vol.101 , pp. 3219-3232
    • Cheng, R.P.1    Gellman, S.H.2    DeGrado, W.F.3
  • 11
    • 0037136471 scopus 로고    scopus 로고
    • Synthesis and 12-helical secondary structure of β-peptides containing (2R, 3R)-aminoproline
    • Porter EA, Wang XF, Schmitt MA, Gellman SH. Synthesis and 12-helical secondary structure of β-peptides containing (2R, 3R)-aminoproline. Org. Lett. 2002; 4: 3317-3319.
    • (2002) Org. Lett. , vol.4 , pp. 3317-3319
    • Porter, E.A.1    Wang, X.F.2    Schmitt, M.A.3    Gellman, S.H.4
  • 12
    • 0030953890 scopus 로고    scopus 로고
    • Design of a novel secondary structure scaffolding device: Induction of a reverse turn in tetrapeptides by incorporating a β-amino acid and stereocontrolled free radical α-substitution reactions in peptide motifs
    • Hanessian S, Yang H. Design of a novel secondary structure scaffolding device: Induction of a reverse turn in tetrapeptides by incorporating a β-amino acid and stereocontrolled free radical α-substitution reactions in peptide motifs. Tetrahedron Lett. 1997; 38: 3155-3158.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 3155-3158
    • Hanessian, S.1    Yang, H.2
  • 13
    • 0032569174 scopus 로고    scopus 로고
    • Design of secondary structures in unnatural peptides: Stable helical γ-tetra-, hexa-, and octapeptides and consequences of α-substitution
    • Hanessian S, Luo X, Schaum R, Michnick S. Design of secondary structures in unnatural peptides: Stable helical γ-tetra-, hexa-, and octapeptides and consequences of α-substitution. J. Am. Chem. Soc. 1998; 120: 8569-8570.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 8569-8570
    • Hanessian, S.1    Luo, X.2    Schaum, R.3    Michnick, S.4
  • 15
    • 0035382627 scopus 로고    scopus 로고
    • The outstanding biological stability of β- and γ-peptides toward proteolytic enzymes: An in vitro investigation with fifteen peptidases
    • Frackenpohl J, Arvidsson PI, Schreiber JV, Seebach D. The outstanding biological stability of β- and γ-peptides toward proteolytic enzymes: An in vitro investigation with fifteen peptidases. ChemBioChem 2001; 2: 445-455.
    • (2001) ChemBioChem. , vol.2 , pp. 445-455
    • Frackenpohl, J.1    Arvidsson, P.I.2    Schreiber, J.V.3    Seebach, D.4
  • 17
    • 0033215517 scopus 로고    scopus 로고
    • Synthesis of enantiomerically pure β- and γ-amino acid derivatives using funtionalized organozinc reagents
    • Dexter CS, Jackson RFW, Elliott J. Synthesis of enantiomerically pure β- and γ-amino acid derivatives using funtionalized organozinc reagents. J. Org. Chem. 1999; 64: 7579-7585.
    • (1999) J. Org. Chem. , vol.64 , pp. 7579-7585
    • Dexter, C.S.1    Jackson, R.F.W.2    Elliott, J.3
  • 18
    • 0031032162 scopus 로고    scopus 로고
    • 1,3-Asymmetric induction in enolate alkylation reactions of N-protected γ-amino acid derivatives
    • Hanessian S, Schaum R. 1,3-Asymmetric induction in enolate alkylation reactions of N-protected γ-amino acid derivatives. Tetrahedron Lett. 1997; 38: 163-166.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 163-166
    • Hanessian, S.1    Schaum, R.2
  • 19
    • 0030822243 scopus 로고    scopus 로고
    • Facile stereoselective synthesis of γ-substituted γ-amino acids from the corresponding α-amino acids
    • Smrcina M, Majer P, Majerová E, Guerassina TA, Eissenstat MA. Facile stereoselective synthesis of γ-substituted γ-amino acids from the corresponding α-amino acids. Tetrahedron 1997; 53: 12867-12874.
    • (1997) Tetrahedron , vol.53 , pp. 12867-12874
    • Smrcina, M.1    Majer, P.2    Majerová, E.3    Guerassina, T.A.4    Eissenstat, M.A.5
  • 20
    • 0037768402 scopus 로고
    • Optically active N-protected α-amino aldehydes in organic synthesis
    • Jurczak J, Golebiowski A. Optically active N-protected α-amino aldehydes in organic synthesis. Chem. Rev. 1989; 89: 149-164.
    • (1989) Chem. Rev. , vol.89 , pp. 149-164
    • Jurczak, J.1    Golebiowski, A.2
  • 21
    • 0032575218 scopus 로고    scopus 로고
    • Effective and mild method for preparation of optically active α-amino aldehydes via TEMPO oxidation
    • Jurczak J, Kobrzycka E, Gruza H, Prokopowicz P. Effective and mild method for preparation of optically active α-amino aldehydes via TEMPO oxidation. Tetrahedron 1998; 54: 6051-6064.
    • (1998) Tetrahedron , vol.54 , pp. 6051-6064
    • Jurczak, J.1    Kobrzycka, E.2    Gruza, H.3    Prokopowicz, P.4
  • 22
    • 85077981913 scopus 로고
    • A convenient one-pot conversion of N-protected amino acids and peptides into alcohols
    • Kokotos G. A convenient one-pot conversion of N-protected amino acids and peptides into alcohols. Synthesis 1990; 299-301.
    • (1990) Synthesis , pp. 299-301
    • Kokotos, G.1
  • 23
    • 0000524914 scopus 로고    scopus 로고
    • Selective one-pot conversion of carboxylic acids into alcohols
    • Kokotos G, Noula C. Selective one-pot conversion of carboxylic acids into alcohols. J. Org. Chem. 1996; 61: 6994-6996.
    • (1996) J. Org. Chem. , vol.61 , pp. 6994-6996
    • Kokotos, G.1    Noula, C.2
  • 24
    • 0026669060 scopus 로고
    • Synthesis of α-amino and α-alkoxy aldehydes via oxoammonium oxidation
    • Leanna MR, Sowin TJ, Morton HE. Synthesis of α-amino and α-alkoxy aldehydes via oxoammonium oxidation. Tetrahedron Lett. 1992; 33: 5029-5032.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 5029-5032
    • Leanna, M.R.1    Sowin, T.J.2    Morton, H.E.3
  • 25
    • 0000290698 scopus 로고
    • Organic oxoammonium salts. A new convenient method for the oxidation of alcohols to aldehydes and ketones
    • Ma Z, Bobbitt JM. Organic oxoammonium salts. A new convenient method for the oxidation of alcohols to aldehydes and ketones. J. Org. Chem. 1991; 56: 6110-6114.
    • (1991) J. Org. Chem. , vol.56 , pp. 6110-6114
    • Ma, Z.1    Bobbitt, J.M.2
  • 26
    • 0000117881 scopus 로고    scopus 로고
    • On the stabilization of the syn-rotamer of amino acid carbamate derivatives by hydrogen bonding
    • Marcovici-Mizrahi D, Gottlieb HE, Marks V, Nudelman A. On the stabilization of the syn-rotamer of amino acid carbamate derivatives by hydrogen bonding. J. Org. Chem. 1996; 61: 8402-8406.
    • (1996) J. Org. Chem. , vol.61 , pp. 8402-8406
    • Marcovici-Mizrahi, D.1    Gottlieb, H.E.2    Marks, V.3    Nudelman, A.4
  • 27
    • 0010640653 scopus 로고
    • α-Methoxy-α-trifluorom-ethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines
    • Dale JA, Dull DL, Mosher H. α-Methoxy-α-trifluorom-ethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J. Org. Chem. 1969; 34: 2543-2549.
    • (1969) J. Org. Chem. , vol.34 , pp. 2543-2549
    • Dale, J.A.1    Dull, D.L.2    Mosher, H.3
  • 28
    • 0013517695 scopus 로고
    • Reaction of sodium hydride with ω-hydroxyalkyl-phosphonium, -arsonium and -ammonium salts
    • Hands AR, Mercer AJ. Reaction of sodium hydride with ω-hydroxyalkyl-phosphonium, -arsonium and -ammonium salts. J. Chem. Soc. 1968; 1331-1337.
    • (1968) J. Chem. Soc. , pp. 1331-1337
    • Hands, A.R.1    Mercer, A.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.