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Volumn 18, Issue 3, 2012, Pages 163-169

Stereoselective synthesis of fully protected (2S,4S,6S)-2-amino-6-hydroxy-4-methyl-8-oxodecanoic acid (AHMOD)

Author keywords

AHMOD; Amino acids; Peptaibiotics; Stereoselectivity; Synthesis

Indexed keywords

1 IODO 4 (TERT BUTYLDIMETHYLSILYLOXY) 2 BUTENE; 2 AMINO 6 HYDROXY 4 METHYL 8 OXODECANOIC ACID; AMINO ACID; GLUTAMIC ACID DERIVATIVE; METHYL 6 (BENZYLOXY) 2 (TERT BUTOXYCARBONYLAMINO) 4 METHYL 8 OXODECANOATE; TERT BUTYL 4 (4 HYDROXY 2 METHYLHEX 5 ENYL) 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; TERT BUTYL 4 (6 HYDROXY 2 METHYLHEX 4 ENYL) 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; TERT BUTYL 4 [2 (4 BENZYL 2 OXOOXAZOLIDINE 3 CARBONYL) 6 (TERT BUTYLDIMETHYLSILYLOXY)HEX 4 ENYL] 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; TERT BUTYL 4 [3 (4 BENZYL 2 OXOOXAZOLIDIN 3 YL) 3 OXOPROPYL] 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; TERT BUTYL 4 [3 [3 (HYDROXYMETHYL)OXIRAN 2 YL] 2 METHYLPROPYL] 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; TERT BUTYL 4 [4 (BENZYLOXY) 2 METHYLHEX 5 ENYL] 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; TERT BUTYL 4 [4 (BENZYLOXY) 6 HYDROXY 2 METHYLHEXYL] 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; TERT BUTYL 4 [4 (BENZYLOXY) 6 HYDROXY 2 METHYLOCTYL] 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; TERT BUTYL 4 [6 (TERT BUTYLDIMETHYLSILYLOXY) 2 (HYDROXYMETHYL)HEX 4 ENYL] 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; UNCLASSIFIED DRUG;

EID: 84862806663     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1433     Document Type: Article
Times cited : (9)

References (33)
  • 1
    • 0345169949 scopus 로고    scopus 로고
    • Brückner H (ed.). European Peptide Society and John Wiley & Sons, Ltd: Chichester, UK
    • In Journal of Peptide Science, Vol. 9, Brückner H (ed.). European Peptide Society and John Wiley & Sons, Ltd: Chichester, UK, 2003; 659-837.
    • (2003) Journal of Peptide Science , vol.9 , pp. 659-837
  • 2
    • 34447536548 scopus 로고    scopus 로고
    • Toniolo C, Brückner, H (eds.). Wiley-VCH: Zürich, Switzerland
    • In Chemistry & Biodiversity, Vol. 4, Toniolo C, Brückner, H (eds.). Wiley-VCH: Zürich, Switzerland, 2007; 1021-1412.
    • (2007) Chemistry & Biodiversity , vol.4 , pp. 1021-1412
  • 5
    • 0032796762 scopus 로고    scopus 로고
    • Isolation and structural elucidation of new peptaibols, bergofungins B, C and D, from Emericellopsis donezkii HKI 0059
    • Berg A, Schlegel B, Ihn W, Demuth U, Gräfe U. Isolation and structural elucidation of new peptaibols, bergofungins B, C and D, from Emericellopsis donezkii HKI 0059. J. Antibiot. 1999; 52: 666-669.
    • (1999) J. Antibiot. , vol.52 , pp. 666-669
    • Berg, A.1    Schlegel, B.2    Ihn, W.3    Demuth, U.4    Gräfe, U.5
  • 6
    • 0033753919 scopus 로고    scopus 로고
    • Two unprecedented natural Aib-peptides with the (Xaa-Yaa-Aib-Pro) motif and an unusual C-terminus: structures, membrane-modifying and antibacterial properties of pseudokonins KL III and KL VI from the fungus Trichoderma pseudokoningii
    • Rebuffat S, Goulard C, Hlimi S, Bodo B. Two unprecedented natural Aib-peptides with the (Xaa-Yaa-Aib-Pro) motif and an unusual C-terminus: structures, membrane-modifying and antibacterial properties of pseudokonins KL III and KL VI from the fungus Trichoderma pseudokoningii. J. Pept. Sci. 2000; 6: 519-533.
    • (2000) J. Pept. Sci. , vol.6 , pp. 519-533
    • Rebuffat, S.1    Goulard, C.2    Hlimi, S.3    Bodo, B.4
  • 7
    • 0028825170 scopus 로고
    • Trichorzins HA and MA, antibiotic peptides from Trichoderma harzianum. I. Fermentation, isolation and biological properties
    • Goulard C, Hlimi S, Refuffat S, Bodo B. Trichorzins HA and MA, antibiotic peptides from Trichoderma harzianum. I. Fermentation, isolation and biological properties. J. Antibiot. 1995; 48: 1248-1253.
    • (1995) J. Antibiot. , vol.48 , pp. 1248-1253
    • Goulard, C.1    Hlimi, S.2    Refuffat, S.3    Bodo, B.4
  • 8
    • 71049165116 scopus 로고    scopus 로고
    • Occurrence and characterization of peptaibols from Trichoderma citrinoviride, an endophytic fungus of cork oak, using electrospray ionization quadrupole time-of-flight mass spectrometry
    • Maddau L, Cabras A, Franceschini A, Linaldeddu BT, Crobu S, Roggio T, Pagnozzi D. Occurrence and characterization of peptaibols from Trichoderma citrinoviride, an endophytic fungus of cork oak, using electrospray ionization quadrupole time-of-flight mass spectrometry. Microbiology 2009; 155: 3371-3381.
    • (2009) Microbiology , vol.155 , pp. 3371-3381
    • Maddau, L.1    Cabras, A.2    Franceschini, A.3    Linaldeddu, B.T.4    Crobu, S.5    Roggio, T.6    Pagnozzi, D.7
  • 9
    • 33847336822 scopus 로고    scopus 로고
    • Proteolytic activity and antibiotic production by Trichoderma harzianum in relation to pathogenicity to insects
    • Shakeri J, Foster HA. Proteolytic activity and antibiotic production by Trichoderma harzianum in relation to pathogenicity to insects. Enzyme Microb. Tech. 2007; 40: 961-968.
    • (2007) Enzyme Microb. Tech. , vol.40 , pp. 961-968
    • Shakeri, J.1    Foster, H.A.2
  • 10
    • 0033868405 scopus 로고    scopus 로고
    • Heptaibin, a novel antifungal peptaibol antibiotic from Emericellopsis sp. BAUA8289
    • Ishiyama D, Satou T, Senda H, Fujimaki T, Honda R, Kanazawa S. Heptaibin, a novel antifungal peptaibol antibiotic from Emericellopsis sp. BAUA8289. J. Antibiot. 2000; 53: 728-732.
    • (2000) J. Antibiot. , vol.53 , pp. 728-732
    • Ishiyama, D.1    Satou, T.2    Senda, H.3    Fujimaki, T.4    Honda, R.5    Kanazawa, S.6
  • 11
    • 0029820049 scopus 로고    scopus 로고
    • Isolation and structure of bergofungin, a new antifungal peptaibol from Emericellopsis donezkii HKI 0059
    • Berg A, Rigzua M, Ihn W, Schlegel B, Fleck WF, Heinze S, Gräfe U. Isolation and structure of bergofungin, a new antifungal peptaibol from Emericellopsis donezkii HKI 0059. J. Antibiot. 1996; 49: 817-820.
    • (1996) J. Antibiot. , vol.49 , pp. 817-820
    • Berg, A.1    Rigzua, M.2    Ihn, W.3    Schlegel, B.4    Fleck, W.F.5    Heinze, S.6    Gräfe, U.7
  • 13
    • 0033826629 scopus 로고    scopus 로고
    • Antiviral activity of antibiotic peptaibols, chrysospemins B and D, produced by Apiocrea sp. 14T against TMV infection
    • Kim YH, Yeo WH, Kim YS, Chae SY, Kim KS. Antiviral activity of antibiotic peptaibols, chrysospemins B and D, produced by Apiocrea sp. 14T against TMV infection. J. Microbiol. Biotechnol. 2000; 10: 522-528.
    • (2000) J. Microbiol. Biotechnol. , vol.10 , pp. 522-528
    • Kim, Y.H.1    Yeo, W.H.2    Kim, Y.S.3    Chae, S.Y.4    Kim, K.S.5
  • 15
    • 0035089485 scopus 로고    scopus 로고
    • Sequences and antimycoplasmic properties of longibrachins LGB II and LGB III, two novel 20-residue peptaibols from Trichoderma longibrachiatum
    • Leclerc G, Goulard C, Prigent Y, Bodo B, Wroblewski H, Rebuffat S. Sequences and antimycoplasmic properties of longibrachins LGB II and LGB III, two novel 20-residue peptaibols from Trichoderma longibrachiatum. J. Nat. Prod. 2001; 64: 164-170.
    • (2001) J. Nat. Prod. , vol.64 , pp. 164-170
    • Leclerc, G.1    Goulard, C.2    Prigent, Y.3    Bodo, B.4    Wroblewski, H.5    Rebuffat, S.6
  • 16
    • 0032562961 scopus 로고    scopus 로고
    • Membrane permeabilisation and antimycoplasmic activity of the 18-residue peptaibols, trichorzins PA
    • Beven L, Duval D, Rebuffat S, Riddell FG, Bodo B, Wroblewski H. Membrane permeabilisation and antimycoplasmic activity of the 18-residue peptaibols, trichorzins PA. BBA-Biomembranes 1998; 1372: 78-90.
    • (1998) BBA-Biomembranes , vol.1372 , pp. 78-90
    • Beven, L.1    Duval, D.2    Rebuffat, S.3    Riddell, F.G.4    Bodo, B.5    Wroblewski, H.6
  • 17
  • 18
    • 0026066649 scopus 로고
    • A comparative study on interactions of alpha-aminoisobutyric acid containing antibiotic peptides, trichopolyn I and hypelcin A with phosphatidylcholine bilayers
    • Matsuzaki K, Shioyama T, Okamura E, Umemura J, Takenaka T, Takaishi T, Fujita T, Miyajima K. A comparative study on interactions of alpha-aminoisobutyric acid containing antibiotic peptides, trichopolyn I and hypelcin A with phosphatidylcholine bilayers. Biochim. Biophys. Acta 1991; 1070: 419-428.
    • (1991) Biochim. Biophys. Acta , vol.1070 , pp. 419-428
    • Matsuzaki, K.1    Shioyama, T.2    Okamura, E.3    Umemura, J.4    Takenaka, T.5    Takaishi, T.6    Fujita, T.7    Miyajima, K.8
  • 19
    • 0025306240 scopus 로고
    • Dual inhibitory effects of the peptide antibiotics leucinostatins on oxidative phosphorylation in mitochondria
    • Shima A, Fukushima K, Arai T, Terada H. Dual inhibitory effects of the peptide antibiotics leucinostatins on oxidative phosphorylation in mitochondria. Cell Struct. Funct. 1990; 15: 53-58.
    • (1990) Cell Struct. Funct. , vol.15 , pp. 53-58
    • Shima, A.1    Fukushima, K.2    Arai, T.3    Terada, H.4
  • 20
    • 0030973663 scopus 로고    scopus 로고
    • Clonostachin, a novel peptaibol that inhibits platelet aggregation
    • Chikanishi T, Hasumi K, Harada T, Kawasaki N, Endo A. Clonostachin, a novel peptaibol that inhibits platelet aggregation. J. Antibiot. 1997; 50: 105-110.
    • (1997) J. Antibiot. , vol.50 , pp. 105-110
    • Chikanishi, T.1    Hasumi, K.2    Harada, T.3    Kawasaki, N.4    Endo, A.5
  • 21
    • 0345169924 scopus 로고    scopus 로고
    • Self-assembling and membrane modifying properties of a lipopeptaibol studied by CW-ESR and PELDOR spectroscopies
    • Milov AD, Tsvetkov YD, Formaggio F, Crisma M, Toniolo C, Raap J. Self-assembling and membrane modifying properties of a lipopeptaibol studied by CW-ESR and PELDOR spectroscopies. J. Pept. Sci. 2003; 9: 690-700.
    • (2003) J. Pept. Sci. , vol.9 , pp. 690-700
    • Milov, A.D.1    Tsvetkov, Y.D.2    Formaggio, F.3    Crisma, M.4    Toniolo, C.5    Raap, J.6
  • 24
    • 78649899857 scopus 로고    scopus 로고
    • Toniolo C, Brückner H (eds.).Wiley-VCH/VHCA: Weinheim/Zürich
    • Degenkolb T, Brückner H. In Peptaibiotics, Toniolo C, Brückner H (eds.).Wiley-VCH/VHCA: Weinheim/Zürich, 2009; 3-29.
    • (2009) Peptaibiotics , pp. 3-29
    • Degenkolb, T.1    Brückner, H.2
  • 25
    • 33745767262 scopus 로고    scopus 로고
    • Culicinin D, an antitumor peptaibol produced by the fungus Culicinomyces clavisporus, strain LL-12I252
    • He H, Janso JE, Yang HY, Berna VS, Lin SL, Yu K. Culicinin D, an antitumor peptaibol produced by the fungus Culicinomyces clavisporus, strain LL-12I252. J. Nat. Prod. 2006; 69: 736-741.
    • (2006) J. Nat. Prod. , vol.69 , pp. 736-741
    • He, H.1    Janso, J.E.2    Yang, H.Y.3    Berna, V.S.4    Lin, S.L.5    Yu, K.6
  • 26
    • 0020417114 scopus 로고
    • Structure of leucinostatin A, new peptide antibiotic from Paecilomyces lilacinus A-267
    • Mori Y, Tsuboi M, Suzuki M, Fukushima K, Arai T. Structure of leucinostatin A, new peptide antibiotic from Paecilomyces lilacinus A-267. J. Chem. Soc. Chem. Commun. 1982; 2: 94-96.
    • (1982) J. Chem. Soc. Chem. Commun. , vol.2 , pp. 94-96
    • Mori, Y.1    Tsuboi, M.2    Suzuki, M.3    Fukushima, K.4    Arai, T.5
  • 27
    • 0033590280 scopus 로고    scopus 로고
    • Peptidic immunosuppressants from the fungus Trichoderma polysporum
    • Iida A, Mihara T, Fujita T, Takaishi Y. Peptidic immunosuppressants from the fungus Trichoderma polysporum. Bioorg. Med. Chem. Lett. 1999; 9: 3393-3396.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 3393-3396
    • Iida, A.1    Mihara, T.2    Fujita, T.3    Takaishi, Y.4
  • 28
    • 0034008515 scopus 로고    scopus 로고
    • Roseoferin, a new aminolipopeptide antibiotic complex from Mycogone rosea DSM 12973, structures and biological activities
    • Degenkolb T, Heinze S, Schlegel B, Dornberger K, Mollmann U, Dahse HM, Gräfe U. Roseoferin, a new aminolipopeptide antibiotic complex from Mycogone rosea DSM 12973, structures and biological activities. J. Antibiot. 2000; 53: 184-190.
    • (2000) J. Antibiot. , vol.53 , pp. 184-190
    • Degenkolb, T.1    Heinze, S.2    Schlegel, B.3    Dornberger, K.4    Mollmann, U.5    Dahse, H.M.6    Gräfe, U.7
  • 29
    • 0025819708 scopus 로고
    • Synthesis of (2S, 4S, 6S)-2-amino-6-hydroxy-4-methyl-8 oxodecanoic acid and (4S, E)-4-methylhex-2-enoic acid constituents of leucinostatines
    • Hadrami ME, Lavergne JP, Viallefont P. Synthesis of (2S, 4S, 6S)-2-amino-6-hydroxy-4-methyl-8 oxodecanoic acid and (4S, E)-4-methylhex-2-enoic acid constituents of leucinostatines. Tetrahedron Lett. 1991; 32: 3985-3988.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3985-3988
    • Hadrami, M.E.1    Lavergne, J.P.2    Viallefont, P.3
  • 30
    • 79960418046 scopus 로고    scopus 로고
    • An improved synthesis of (2S, 4S)- and (2S, 4R)-2-amino-4-methyl decanoic acids: an evidence of the stereochemistry of culicinins
    • Zhang W, Ding N, Li Y. An improved synthesis of (2S, 4S)- and (2S, 4R)-2-amino-4-methyl decanoic acids: an evidence of the stereochemistry of culicinins. J. Pept. Sci. 2011; 17: 576-580.
    • (2011) J. Pept. Sci. , vol.17 , pp. 576-580
    • Zhang, W.1    Ding, N.2    Li, Y.3
  • 32
    • 0001172890 scopus 로고
    • Reactions of 2,3-epoxyhalides. Synthesis of optically active allylic alcohols and homoallylic epoxides
    • Nicolaou KC, Duggan ME, Ladduwahetty T. Reactions of 2, 3-epoxyhalides. Synthesis of optically active allylic alcohols and homoallylic epoxides. Tetrahedron Lett. 1984; 25: 2069-2072.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 2069-2072
    • Nicolaou, K.C.1    Duggan, M.E.2    Ladduwahetty, T.3
  • 33
    • 33646164915 scopus 로고    scopus 로고
    • Enantioselective total synthesis of bistramide A
    • Crimmins MT, DeBaillie AC. Enantioselective total synthesis of bistramide A. J. Am. Chem. Soc. 2006; 128: 4936-4937.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 4936-4937
    • Crimmins, M.T.1    DeBaillie, A.C.2


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