메뉴 건너뛰기




Volumn 16, Issue 4, 2010, Pages 267-275

Synthesis of Hybrid Peptidomimetics and Neoglycoconjugates Employing Click Protocol: Dual utility of Poc-group for inserting carbamate-triazole units into peptide backbone

Author keywords

1,2,3 triazole; Carbamate; Click chemistry; Hybrid mimetics; Peptidomimetics; Poc group

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; AMINO ACID; AMINOSUGAR; AZIDE; CARBAMIC ACID DERIVATIVE; PEPTIDOMIMETIC AGENT;

EID: 78649685977     PISSN: 15733149     EISSN: 15733904     Source Type: Journal    
DOI: 10.1007/s10989-010-9228-6     Document Type: Article
Times cited : (5)

References (56)
  • 1
    • 27744447259 scopus 로고    scopus 로고
    • Ring closure to β-turn mimics via copper-catalyzed azide/alkyne cycloadditions
    • 1:CAS:528:DC%2BD2MXhtFahs7zE 10.1021/jo0516180 16268639
    • Y Angell K Burgess 2005 Ring closure to β-turn mimics via copper-catalyzed azide/alkyne cycloadditions J Org Chem 70 9595 9598 1:CAS:528:DC%2BD2MXhtFahs7zE 10.1021/jo0516180 16268639
    • (2005) J Org Chem , vol.70 , pp. 9595-9598
    • Angell, Y.1    Burgess, K.2
  • 2
    • 29044447377 scopus 로고    scopus 로고
    • Nonpeptidic foldamers from amino acids: Synthesis and characterization of 1,3-substituted triazole oligomers
    • 1:CAS:528:DC%2BD2MXht1Smt7rL 10.1021/ja056406z 16332031
    • NG Angelo PS Arora 2005 Nonpeptidic foldamers from amino acids: synthesis and characterization of 1,3-substituted triazole oligomers J Am Chem Soc 127 17134 17135 1:CAS:528:DC%2BD2MXht1Smt7rL 10.1021/ja056406z 16332031
    • (2005) J Am Chem Soc , vol.127 , pp. 17134-17135
    • Angelo, N.G.1    Arora, P.S.2
  • 3
    • 0037170609 scopus 로고    scopus 로고
    • Synthesis and applications of propargyl pentafluorophenyl carbonate for peptide synthesis
    • 1:CAS:528:DC%2BD38XhvFOnu7w%3D 10.1016/S0040-4039(02)00287-3
    • RG Bhat E Kerouredan E Porhiel S Chandrasekaran 2002 Synthesis and applications of propargyl pentafluorophenyl carbonate for peptide synthesis Tetrahedron Lett 43 2467 2469 1:CAS:528:DC%2BD38XhvFOnu7w%3D 10.1016/S0040-4039(02)00287-3
    • (2002) Tetrahedron Lett , vol.43 , pp. 2467-2469
    • Bhat, R.G.1    Kerouredan, E.2    Porhiel, E.3    Chandrasekaran, S.4
  • 4
    • 33644935644 scopus 로고    scopus 로고
    • Click chemistry as a route to cyclic tetrapeptide analogues: Synthesis of cyclo-[Pro-Val-ψ(triazole)-Pro-Tyr]
    • 1:CAS:528:DC%2BD28Xht1ajtbY%3D 10.1021/ol053095o 16494474
    • VD Bock R Perciaccante TP Jansen H Hiemstra JH van Maarseveen 2006 Click chemistry as a route to cyclic tetrapeptide analogues: synthesis of cyclo-[Pro-Val-ψ(triazole)-Pro-Tyr] Org Lett 8 919 922 1:CAS:528: DC%2BD28Xht1ajtbY%3D 10.1021/ol053095o 16494474
    • (2006) Org Lett , vol.8 , pp. 919-922
    • Bock, V.D.1    Perciaccante, R.2    Jansen, T.P.3    Hiemstra, H.4    Van Maarseveen, J.H.5
  • 5
    • 33847733975 scopus 로고    scopus 로고
    • 1,2,3-Triazoles as peptide bond isosters: Synthesis and biological evaluation of cyclotetrapeptide mimics
    • 1:CAS:528:DC%2BD2sXisV2gtL8%3D 10.1039/b616751a 17340013
    • VD Bock D Speijer H Hiemstra JH van Maarseveen 2007 1,2,3-Triazoles as peptide bond isosters: synthesis and biological evaluation of cyclotetrapeptide mimics Org Biomol Chem 5 971 975 1:CAS:528:DC%2BD2sXisV2gtL8%3D 10.1039/b616751a 17340013
    • (2007) Org Biomol Chem , vol.5 , pp. 971-975
    • Bock, V.D.1    Speijer, D.2    Hiemstra, H.3    Van Maarseveen, J.H.4
  • 6
    • 22144498399 scopus 로고    scopus 로고
    • 1,2,3-Triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors
    • 1:CAS:528:DC%2BD2MXms12ktb0%3D 15934050
    • A Brik J Alexandratos Y-C Lin JH Elder AJ Olson A Wlodawer DS Goodsell C-H Wong 2005 1,2,3-Triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors Chem Bio Chem 6 1167 1169 1:CAS:528: DC%2BD2MXms12ktb0%3D 15934050
    • (2005) Chem Bio Chem , vol.6 , pp. 1167-1169
    • Brik, A.1    Alexandratos, J.2    Lin, Y.-C.3    Elder, J.H.4    Olson, A.J.5    Wlodawer, A.6    Goodsell, D.S.7    Wong, C.-H.8
  • 7
    • 71849111550 scopus 로고    scopus 로고
    • Development and characterization of lysine based tripeptide analogues as inhibitors of Sir2 activity
    • 1:CAS:528:DC%2BD1MXhtl2js7bJ 10.1016/j.bmc.2009.10.003 19861237
    • SP Chakrabarty R Ramapanicker R Mishra S Chandrasekaran H Balaram 2009 Development and characterization of lysine based tripeptide analogues as inhibitors of Sir2 activity Bioorg Med Chem 17 8060 8072 1:CAS:528: DC%2BD1MXhtl2js7bJ 10.1016/j.bmc.2009.10.003 19861237
    • (2009) Bioorg Med Chem , vol.17 , pp. 8060-8072
    • Chakrabarty, S.P.1    Ramapanicker, R.2    Mishra, R.3    Chandrasekaran, S.4    Balaram, H.5
  • 10
    • 33947493431 scopus 로고    scopus 로고
    • I-catalysed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry
    • 1:CAS:528:DC%2BD2sXjt1Squ7k%3D 10.1039/b618048p 17377651
    • I-catalysed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry Org Biomol Chem 5 1006 1017 1:CAS:528: DC%2BD2sXjt1Squ7k%3D 10.1039/b618048p 17377651
    • (2007) Org Biomol Chem , vol.5 , pp. 1006-1017
    • Dedola, S.1    Nepogodiev, S.A.2    Field, R.A.3
  • 11
    • 33745700325 scopus 로고    scopus 로고
    • Sonochemistry: A powerful way of enhancing the efficiency of carbohydrate synthesis
    • 1:CAS:528:DC%2BD28XlvFent7Y%3D 10.1021/jo060374w 16808504
    • S Deng U Gangadharmath C-WT Chang 2006 Sonochemistry: a powerful way of enhancing the efficiency of carbohydrate synthesis J Org Chem 71 5179 5185 1:CAS:528:DC%2BD28XlvFent7Y%3D 10.1021/jo060374w 16808504
    • (2006) J Org Chem , vol.71 , pp. 5179-5185
    • Deng, S.1    Gangadharmath, U.2    C-Wt, C.3
  • 12
    • 0035312947 scopus 로고    scopus 로고
    • Chemical synthesis of linear and cyclic unnatural oligosaccharides by iterartive glycosidation of ketoses
    • 1:CAS:528:DC%2BD3MXis1Oqtbc%3D 10.1002/1521-3765(20010401)7:7<1371:: AID-CHEM1371>3.0.CO;2-J
    • A Dondoni A Marra M-C Scherrmann V Bertolasi 2001 Chemical synthesis of linear and cyclic unnatural oligosaccharides by iterartive glycosidation of ketoses Chem Eur J 7 1371 1382 1:CAS:528:DC%2BD3MXis1Oqtbc%3D 10.1002/1521-3765(20010401)7:7<1371::AID-CHEM1371>3.0.CO;2-J
    • (2001) Chem Eur J , vol.7 , pp. 1371-1382
    • Dondoni, A.1    Marra, A.2    Scherrmann, M.-C.3    Bertolasi, V.4
  • 13
    • 0542421525 scopus 로고    scopus 로고
    • Foldamers: A manifesto
    • 1:CAS:528:DyaK1cXhvF2qtr0%3D 10.1021/ar960298r
    • SH Gellman 1998 Foldamers: a manifesto Acc Chem Res 31 173 180 1:CAS:528:DyaK1cXhvF2qtr0%3D 10.1021/ar960298r
    • (1998) Acc Chem Res , vol.31 , pp. 173-180
    • Gellman, S.H.1
  • 14
    • 34250353931 scopus 로고    scopus 로고
    • Click chemistry-what's in name? Triazole synthesis and beyond
    • 10.1055/s-2007-966071
    • MV Gil MJ Arevalo O Lopez 2007 Click chemistry-what's in name? Triazole synthesis and beyond Synthesis 11 1589 1620 10.1055/s-2007-966071
    • (2007) Synthesis , vol.11 , pp. 1589-1620
    • Gil, M.V.1    Arevalo, M.J.2    Lopez, O.3
  • 15
    • 78649664000 scopus 로고    scopus 로고
    • Synthesis of peptides and peptidomimetics (Houben-Weyl) Stuttgart and references cited therein
    • Goodman M, Felix A, Moroder L, Toniolo C (eds) (2003) Synthesis of peptides and peptidomimetics (Houben-Weyl). Georg Thieme Verlag, Stuttgart, vol E22c and references cited therein
    • (2003) Georg Thieme Verlag , vol.22 C
    • Goodman, M.1    Felix, A.2    Moroder, L.3    Toniolo, C.4
  • 16
    • 75749138516 scopus 로고    scopus 로고
    • From peptides to their alternating ester-urea analogues: Synthesis and influence of hydrogen bonding motif and stereochemistry on aggregation
    • 1:CAS:528:DC%2BD1MXhs1WltrbI 10.1021/jo902249w 20039647
    • S Hartwig J Schwarz S Hecht 2010 From peptides to their alternating ester-urea analogues: synthesis and influence of hydrogen bonding motif and stereochemistry on aggregation J Org Chem 75 772 782 1:CAS:528: DC%2BD1MXhs1WltrbI 10.1021/jo902249w 20039647
    • (2010) J Org Chem , vol.75 , pp. 772-782
    • Hartwig, S.1    Schwarz, J.2    Hecht, S.3
  • 17
    • 70350496713 scopus 로고    scopus 로고
    • A simple approach for the synthesis of new classes of dithiocarbamate-linked peptidomimetics
    • 1:CAS:528:DC%2BD1MXhtlGisrrJ 10.1016/j.tetlet.2009.09.172
    • HP Hemantha VV Sureshbabu 2009 A simple approach for the synthesis of new classes of dithiocarbamate-linked peptidomimetics Tetrahedron Lett 50 7062 7066 1:CAS:528:DC%2BD1MXhtlGisrrJ 10.1016/j.tetlet.2009.09.172
    • (2009) Tetrahedron Lett , vol.50 , pp. 7062-7066
    • Hemantha, H.P.1    Sureshbabu, V.V.2
  • 18
    • 0041707953 scopus 로고    scopus 로고
    • A heterocyclic peptide nanotube
    • 1:CAS:528:DC%2BD3sXltF2rtrk%3D 10.1021/ja034358h 12889966
    • WS Horne CD Stout MR Ghadiri 2003 A heterocyclic peptide nanotube J Am Chem Soc 125 9372 9376 1:CAS:528:DC%2BD3sXltF2rtrk%3D 10.1021/ja034358h 12889966
    • (2003) J Am Chem Soc , vol.125 , pp. 9372-9376
    • Horne, W.S.1    Stout, C.D.2    Ghadiri, M.R.3
  • 19
    • 9644268752 scopus 로고    scopus 로고
    • Heterocyclic peptide backbone modifications in an α-helical coiled coil
    • 10.1021/ja0450408
    • WS Horne MK Yadav CD Stout MR Ghadiri 2004 Heterocyclic peptide backbone modifications in an α-helical coiled coil J Am Chem Soc 126 5366 15367 10.1021/ja0450408
    • (2004) J Am Chem Soc , vol.126 , pp. 5366-15367
    • Horne, W.S.1    Yadav, M.K.2    Stout, C.D.3    Ghadiri, M.R.4
  • 20
    • 36749014055 scopus 로고
    • 1,3-Dipolar cycloadditions past and future
    • 10.1002/anie.196305651
    • R Huisgen 1963 1,3-Dipolar cycloadditions past and future Angew Chem Int Ed 2 565 632 10.1002/anie.196305651
    • (1963) Angew Chem Int Ed , vol.2 , pp. 565-632
    • Huisgen, R.1
  • 21
    • 84943927274 scopus 로고
    • Kinetics and mechanism of 1,3-dipolar cycloadditions
    • 10.1002/anie.196306331
    • R Huisgen 1963 Kinetics and mechanism of 1,3-dipolar cycloadditions Angew Chem Int Ed 2 633 696 10.1002/anie.196306331
    • (1963) Angew Chem Int Ed , vol.2 , pp. 633-696
    • Huisgen, R.1
  • 23
    • 0002825957 scopus 로고    scopus 로고
    • Prop-2-ynyl as a protective group for carboxylic acids: A mild method for the highly selective deprotection of prop-2-ynyl esters using tetrathiomolybdate
    • Ilankumaran P, Manoj N, Chandrasekaran S (1996) Prop-2-ynyl as a protective group for carboxylic acids: a mild method for the highly selective deprotection of prop-2-ynyl esters using tetrathiomolybdate. Chem Commun 1957-1958
    • (1996) Chem Commun , pp. 1957-1958
    • Ilankumaran, P.1    Manoj, N.2    Chandrasekaran, S.3
  • 24
    • 0348109450 scopus 로고    scopus 로고
    • The growing impact of click chemistry on drug discovery
    • 1:CAS:528:DC%2BD3sXpvVWkuro%3D 10.1016/S1359-6446(03)02933-7 14678739
    • HC Kolb BK Sharpless 2003 The growing impact of click chemistry on drug discovery Drug Discov Today 8 1128 1137 1:CAS:528:DC%2BD3sXpvVWkuro%3D 10.1016/S1359-6446(03)02933-7 14678739
    • (2003) Drug Discov Today , vol.8 , pp. 1128-1137
    • Kolb, H.C.1    Sharpless, B.K.2
  • 25
    • 0000096835 scopus 로고    scopus 로고
    • Click chemistry: Diverse chemical function from a few good reactions
    • 1:CAS:528:DC%2BD3MXksVOis78%3D 10.1002/1521-3773(20010601)40:11<2004:: AID-ANIE2004>3.0.CO;2-5
    • HC Kolb MG Finn BK Sharpless 2001 Click chemistry: diverse chemical function from a few good reactions Angew Chem Int Ed 40 2004 2021 1:CAS:528:DC%2BD3MXksVOis78%3D 10.1002/1521-3773(20010601)40:11<2004::AID- ANIE2004>3.0.CO;2-5
    • (2001) Angew Chem Int Ed , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, B.K.3
  • 26
    • 18644384979 scopus 로고    scopus 로고
    • In situ selection of lead compounds by click chemistry: Target-guided optimization of acetylcholinesterase inhibitors
    • 1:CAS:528:DC%2BD2MXjtlWkt7c%3D 10.1021/ja043031t 15869290
    • A Krasinski Z Radic R Manetsch J Raushel P Taylor BK Sharpless HC Kolb 2005 In situ selection of lead compounds by click chemistry: target-guided optimization of acetylcholinesterase inhibitors J Am Chem Soc 127 6686 6692 1:CAS:528:DC%2BD2MXjtlWkt7c%3D 10.1021/ja043031t 15869290
    • (2005) J Am Chem Soc , vol.127 , pp. 6686-6692
    • Krasinski, A.1    Radic, Z.2    Manetsch, R.3    Raushel, J.4    Taylor, P.5    Sharpless, B.K.6    Kolb, H.C.7
  • 27
    • 4544344028 scopus 로고    scopus 로고
    • Expedient synthesis triazole-linked glycosyl amino acids and peptides
    • 1:CAS:528:DC%2BD2cXmtFOks74%3D 10.1021/ol048841o 15330603
    • BHM Kuijpers S Groothuys AR Keereweer PJLM Quaedflieg RH Blaauw FL van Delft FPJT Rutjes 2004 Expedient synthesis triazole-linked glycosyl amino acids and peptides Org Lett 6 3123 3126 1:CAS:528:DC%2BD2cXmtFOks74%3D 10.1021/ol048841o 15330603
    • (2004) Org Lett , vol.6 , pp. 3123-3126
    • Kuijpers, B.H.M.1    Groothuys, S.2    Keereweer, A.R.3    Pjlm, Q.4    Blaauw, R.H.5    Van Delft, F.L.6    Fpjt, R.7
  • 28
    • 0025301307 scopus 로고
    • Synthesis of 1-aryl-1,2,3-triazole-4,5-dimethanol-4,5- bis(isopropylcarbamates) as potential antineoplastic agents
    • 1:CAS:528:DyaK3cXlsFagsLc%3D 10.1002/jhet.5570270338
    • I Lalezari LA Gomez M Khorshidi 1990 Synthesis of 1-aryl-1,2,3-triazole- 4,5-dimethanol-4,5-bis(isopropylcarbamates) as potential antineoplastic agents J Heterocyclic Chem 27 687 689 1:CAS:528:DyaK3cXlsFagsLc%3D 10.1002/jhet. 5570270338
    • (1990) J Heterocyclic Chem , vol.27 , pp. 687-689
    • Lalezari, I.1    Gomez, L.A.2    Khorshidi, M.3
  • 29
    • 34948864467 scopus 로고    scopus 로고
    • Efficient synthesis of linear multifunctional poly (ethylene glycol) by copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition
    • 1:CAS:528:DC%2BD2sXoslarsbk%3D 10.1021/bm070430i 17688321
    • X-M Liu A Thakur D Wang 2007 Efficient synthesis of linear multifunctional poly (ethylene glycol) by copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition Biomacromolecules 8 2653 2658 1:CAS:528: DC%2BD2sXoslarsbk%3D 10.1021/bm070430i 17688321
    • (2007) Biomacromolecules , vol.8 , pp. 2653-2658
    • Liu, X.-M.1    Thakur, A.2    Wang, D.3
  • 31
    • 0036007054 scopus 로고    scopus 로고
    • α-Methylene tetrazole-based peptidomimetics: Synthesis and inhibition of HIV protease
    • BCH May AD Abell 2002 α-Methylene tetrazole-based peptidomimetics: synthesis and inhibition of HIV protease J Chem Soc Perkin Trans I 172 178
    • (2002) J Chem Soc Perkin Trans , vol.1 , pp. 172-178
    • May, B.C.H.1    Abell, A.D.2
  • 32
    • 0028912201 scopus 로고
    • Novel biopolymers for drug discovery
    • 1:CAS:528:DyaK2MXksVSntrc%3D 10.1002/bip.360370305 7718743
    • EJ Moran TE Wilson CY Cho SR Cherry PG Schultz 1995 Novel biopolymers for drug discovery Biopolymers 37 213 219 1:CAS:528:DyaK2MXksVSntrc%3D 10.1002/bip.360370305 7718743
    • (1995) Biopolymers , vol.37 , pp. 213-219
    • Moran, E.J.1    Wilson, T.E.2    Cho, C.Y.3    Cherry, S.R.4    Schultz, P.G.5
  • 33
    • 27744455370 scopus 로고    scopus 로고
    • P.E. Nielson (eds). Wiley-VCH Weinheim
    • Nielson PE (ed) (2004) Pseudo-peptides in drug discovery. Wiley-VCH, Weinheim
    • (2004) Pseudo-peptides in Drug Discovery
  • 34
    • 0034689867 scopus 로고    scopus 로고
    • Synthesis of functionalized oxazolins and oxazoles with DST and Deoxo-Fluor
    • 1:CAS:528:DC%2BD3cXhvFKntLk%3D 10.1021/ol005777b 10804580
    • AJ Phillips Y Uto P Wipf MJ Reno DR Williams 2000 Synthesis of functionalized oxazolins and oxazoles with DST and Deoxo-Fluor Org Lett 2 1165 1168 1:CAS:528:DC%2BD3cXhvFKntLk%3D 10.1021/ol005777b 10804580
    • (2000) Org Lett , vol.2 , pp. 1165-1168
    • Phillips, A.J.1    Uto, Y.2    Wipf, P.3    Reno, M.J.4    Williams, D.R.5
  • 35
    • 73349132016 scopus 로고    scopus 로고
    • One-pot protection and activation of amino acids using pentafluorophenyl carbonates
    • 1:CAS:528:DC%2BD1MXhtlOku7zM 10.1002/psc.1187 19856278
    • R Ramapanicker NBR Baig K De S Chandrasekaran 2009 One-pot protection and activation of amino acids using pentafluorophenyl carbonates J Pept Sci 15 849 855 1:CAS:528:DC%2BD1MXhtlOku7zM 10.1002/psc.1187 19856278
    • (2009) J Pept Sci , vol.15 , pp. 849-855
    • Ramapanicker, R.1    Baig, N.B.R.2    De, K.3    Chandrasekaran, S.4
  • 36
    • 27644510884 scopus 로고    scopus 로고
    • 2-symmetric reagent for the protection of amines and amino acids
    • 1:CAS:528:DC%2BD2MXhtVKhsbzP 10.1021/ol051960z 16235929
    • 2-symmetric reagent for the protection of amines and amino acids Org Lett 7 4947 4950 1:CAS:528:DC%2BD2MXhtVKhsbzP 10.1021/ol051960z 16235929
    • (2005) Org Lett , vol.7 , pp. 4947-4950
    • Ramesh, R.1    Chandrasekaran, S.2
  • 37
    • 33646445618 scopus 로고    scopus 로고
    • Simultaneous protection and activation of amino acids using propargyl pentafluorophenyl carbonate
    • 1:CAS:528:DC%2BD28XjtV2ju7s%3D 10.1021/ol060494q 16623588
    • R Ramesh S Rajasekaran R Gupta S Chandrasekaran 2006 Simultaneous protection and activation of amino acids using propargyl pentafluorophenyl carbonate Org Lett 8 1933 1936 1:CAS:528:DC%2BD28XjtV2ju7s%3D 10.1021/ol060494q 16623588
    • (2006) Org Lett , vol.8 , pp. 1933-1936
    • Ramesh, R.1    Rajasekaran, S.2    Gupta, R.3    Chandrasekaran, S.4
  • 38
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise Huisgen cycloaddition process: Copper(I)-catalysed regioselective ligation of azides and terminal alkynes
    • 1:CAS:528:DC%2BD38Xls1Ohsr4%3D 10.1002/1521-3773(20020715)41:14<2596:: AID-ANIE2596>3.0.CO;2-4
    • VV Rostovtsev LG Green VV Fokin BK Sharpless 2002 A stepwise Huisgen cycloaddition process: copper(I)-catalysed regioselective ligation of azides and terminal alkynes Angew Chem Int Ed 41 2596 2599 1:CAS:528:DC%2BD38Xls1Ohsr4%3D 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
    • (2002) Angew Chem Int Ed , vol.41 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, B.K.4
  • 39
    • 57149097169 scopus 로고    scopus 로고
    • β-Peptidic peptidomimetics
    • 1:CAS:528:DC%2BD1cXnvVKksrk%3D 10.1021/ar700263g 18578513
    • D Seebach J Gardiner 2008 β-Peptidic peptidomimetics Acc Chem Res 41 1366 1375 1:CAS:528:DC%2BD1cXnvVKksrk%3D 10.1021/ar700263g 18578513
    • (2008) Acc Chem Res , vol.41 , pp. 1366-1375
    • Seebach, D.1    Gardiner, J.2
  • 40
    • 78649648651 scopus 로고    scopus 로고
    • N. Sewald H-D Jakubke (eds). Wiley-VCH Weinheim
    • Sewald N, Jakubke H-D, (eds) (2002) Peptides: chemistry and biology. Wiley-VCH, Weinheim, p 354
    • (2002) Peptides: Chemistry and Biology , pp. 354
  • 41
    • 0442264158 scopus 로고    scopus 로고
    • Propargyloxycarbonyl (Poc) as a protective group for the hydroxyl function in carbohydrate synthesis
    • 1:CAS:528:DC%2BD38Xpt1ClsL8%3D 10.1021/ol027220x 12489973
    • PR Sridhar S Chandrasekaran 2002 Propargyloxycarbonyl (Poc) as a protective group for the hydroxyl function in carbohydrate synthesis Org Lett 4 4731 4733 1:CAS:528:DC%2BD38Xpt1ClsL8%3D 10.1021/ol027220x 12489973
    • (2002) Org Lett , vol.4 , pp. 4731-4733
    • Sridhar, P.R.1    Chandrasekaran, S.2
  • 42
    • 33749119341 scopus 로고    scopus 로고
    • α- Fmoc-peptide isocyanates: Solution synthesis of oligo-α-peptidyl ureas
    • 1:CAS:528:DC%2BD28Xoslaktr4%3D 10.1021/jo0611723 16995676
    • α-Fmoc-peptide isocyanates: solution synthesis of oligo-α-peptidyl ureas J Org Chem 71 7697 7705 1:CAS:528:DC%2BD28Xoslaktr4%3D 10.1021/jo0611723 16995676
    • (2006) J Org Chem , vol.71 , pp. 7697-7705
    • Sureshbabu, V.V.1    Patil, B.S.2    Venkataramanarao, R.3
  • 43
    • 47049084129 scopus 로고    scopus 로고
    • Synthesis of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics
    • 1:CAS:528:DC%2BD1cXoslekurw%3D 10.1016/j.tetlet.2008.06.091
    • VV Sureshbabu HP Hemantha SA Naik 2008 Synthesis of 1,2,4-oxadiazole- linked orthogonally urethane-protected dipeptide mimetics Tetrahedron Lett 49 5133 5136 1:CAS:528:DC%2BD1cXoslekurw%3D 10.1016/j.tetlet.2008.06.091
    • (2008) Tetrahedron Lett , vol.49 , pp. 5133-5136
    • Sureshbabu, V.V.1    Hemantha, H.P.2    Naik, S.A.3
  • 44
    • 40049087671 scopus 로고    scopus 로고
    • A facile synthesis of C-terminal neoglycopeptides: Incorporation of urea moiety between sugars and peptides employing Curtius rearrangement
    • 1:CAS:528:DC%2BD1cXjsVWlu7k%3D 10.1007/s10989-007-9101-4
    • VV Sureshbabu R Venkataramanarao HP Hemantha 2008 A facile synthesis of C-terminal neoglycopeptides: incorporation of urea moiety between sugars and peptides employing Curtius rearrangement Int J Pept Res Ther 14 34 40 1:CAS:528:DC%2BD1cXjsVWlu7k%3D 10.1007/s10989-007-9101-4
    • (2008) Int J Pept Res Ther , vol.14 , pp. 34-40
    • Sureshbabu, V.V.1    Venkataramanarao, R.2    Hemantha, H.P.3
  • 45
    • 68049103235 scopus 로고    scopus 로고
    • N-Urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization and application to the synthesis of thioureidopeptides
    • 1:CAS:528:DC%2BD1MXnsVeiur8%3D 10.1021/jo900675s 19537728
    • VV Sureshbabu SA Naik HP Hemantha N Narendra U Das TNG Row 2009 N-Urethane-protected amino alkyl isothiocyanates: synthesis, isolation, characterization and application to the synthesis of thioureidopeptides J Org Chem 74 5260 5266 1:CAS:528:DC%2BD1MXnsVeiur8%3D 10.1021/jo900675s 19537728
    • (2009) J Org Chem , vol.74 , pp. 5260-5266
    • Sureshbabu, V.V.1    Naik, S.A.2    Hemantha, H.P.3    Narendra, N.4    Das, U.5    Row, T.N.G.6
  • 46
    • 77749334209 scopus 로고    scopus 로고
    • Glycosylated amino acids and neoglycoconjugates using bis(benzotriazolyl)methanethione as thioacylating agent
    • Synthesis of thioureido-linked peptidomimetics
    • Sureshbabu VV, Chennakrishnareddy G, Hemantha HP (2010) Synthesis of thioureido-linked peptidomimetics, glycosylated amino acids and neoglycoconjugates using bis(benzotriazolyl)methanethione as thioacylating agent. Synlett 715-720
    • (2010) Synlett , pp. 715-720
    • Sureshbabu, V.V.1    Chennakrishnareddy, G.2    Hemantha, H.P.3
  • 47
    • 33646946320 scopus 로고    scopus 로고
    • Synthesis of multivalent lactose derivatives by 1,3-dipolar cycloadditions: Selective galectin-1 inhibition
    • 1:CAS:528:DC%2BD28XlsVyqt7g%3D 10.1016/j.carres.2006.04.028 16697988
    • J Tejler E Tullberg T Frejd H Leffler UJ Nilsson 2006 Synthesis of multivalent lactose derivatives by 1,3-dipolar cycloadditions: selective galectin-1 inhibition Carbohydr Res 341 1353 1362 1:CAS:528:DC%2BD28XlsVyqt7g%3D 10.1016/j.carres.2006.04.028 16697988
    • (2006) Carbohydr Res , vol.341 , pp. 1353-1362
    • Tejler, J.1    Tullberg, E.2    Frejd, T.3    Leffler, H.4    Nilsson, U.J.5
  • 48
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalysed 1,3-dipolar cycloadditions of terminal alkynes to azides
    • 1:CAS:528:DC%2BD38XisVeks7w%3D 10.1021/jo011148j 11975567
    • CW Tornoe C Christensen M Meldal 2002 Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalysed 1,3-dipolar cycloadditions of terminal alkynes to azides J Org Chem 67 3057 3064 1:CAS:528:DC%2BD38XisVeks7w%3D 10.1021/jo011148j 11975567
    • (2002) J Org Chem , vol.67 , pp. 3057-3064
    • Tornoe, C.W.1    Christensen, C.2    Meldal, M.3
  • 49
    • 2542542164 scopus 로고    scopus 로고
    • Combinatorial library of peptidotriazoles: Identification of [1, 2, 3]-triazole inhibitors against a recombinant Leishmania mexicana cysteine protease
    • 1:CAS:528:DC%2BD2cXis1Orurs%3D 10.1021/cc020085v 15132590
    • CW Tornoe SJ Sanderson JC Mottram GH Coombs M Meldal 2004 Combinatorial library of peptidotriazoles: identification of [1, 2, 3]-triazole inhibitors against a recombinant Leishmania mexicana cysteine protease J Comb Chem 6 312 324 1:CAS:528:DC%2BD2cXis1Orurs%3D 10.1021/cc020085v 15132590
    • (2004) J Comb Chem , vol.6 , pp. 312-324
    • Tornoe, C.W.1    Sanderson, S.J.2    Mottram, J.C.3    Coombs, G.H.4    Meldal, M.5
  • 50
    • 44949231073 scopus 로고    scopus 로고
    • Peptidomimetics, a synthetic tool of discovery
    • 1:CAS:528:DC%2BD1cXnt1ersro%3D 10.1016/j.cbpa.2008.03.009 18423417
    • J Vagner H Qu VJ Hruby 2008 Peptidomimetics, a synthetic tool of discovery Curr Opin Chem Biol 12 292 296 1:CAS:528:DC%2BD1cXnt1ersro%3D 10.1016/j.cbpa.2008.03.009 18423417
    • (2008) Curr Opin Chem Biol , vol.12 , pp. 292-296
    • Vagner, J.1    Qu, H.2    Hruby, V.J.3
  • 51
    • 0029739241 scopus 로고    scopus 로고
    • Syntesis of naturally ocurring, conformationally restricted oxazole- and thiazole-containing di- and tripeptides mimetics
    • 1:CAS:528:DyaK28Xkslens70%3D 10.1002/anie.199615031
    • G Videnov D Kaiser C Kempter G Jung 1996 Syntesis of naturally ocurring, conformationally restricted oxazole- and thiazole-containing di- and tripeptides mimetics Angew Chem Int Ed 35 1503 1506 1:CAS:528:DyaK28Xkslens70%3D 10.1002/anie.199615031
    • (1996) Angew Chem Int Ed , vol.35 , pp. 1503-1506
    • Videnov, G.1    Kaiser, D.2    Kempter, C.3    Jung, G.4
  • 52
    • 0031561062 scopus 로고    scopus 로고
    • HIV-1 TAR RNA recognition by unnatural biopolymer
    • 1:CAS:528:DyaK2sXktlKjsbY%3D 10.1021/ja963895h
    • X Wang I Huq TM Rana 1997 HIV-1 TAR RNA recognition by unnatural biopolymer J Am Chem Soc 119 6444 6445 1:CAS:528:DyaK2sXktlKjsbY%3D 10.1021/ja963895h
    • (1997) J Am Chem Soc , vol.119 , pp. 6444-6445
    • Wang, X.1    Huq, I.2    Rana, T.M.3
  • 54
    • 33845939348 scopus 로고    scopus 로고
    • Rapid discovery and structure-activity profiling of novel inhibitors of human immunodeficiency virus type 1 protease enabled by the Copper(I)-catalyzed synthesis of 1,2,3-triazoles and their further functionalization
    • 1:CAS:528:DC%2BD28Xht1GjsbjL 10.1021/jm060754+ 17181152
    • M Whiting JC Tripp Y-C Lin W Lindstorm AJ Olson JH Elder BK Sharpless VV Fokin 2006 Rapid discovery and structure-activity profiling of novel inhibitors of human immunodeficiency virus type 1 protease enabled by the Copper(I)-catalyzed synthesis of 1,2,3-triazoles and their further functionalization J Med Chem 49 7697 7710 1:CAS:528:DC%2BD28Xht1GjsbjL 10.1021/jm060754+ 17181152
    • (2006) J Med Chem , vol.49 , pp. 7697-7710
    • Whiting, M.1    Tripp, J.C.2    Lin, Y.-C.3    Lindstorm, W.4    Olson, A.J.5    Elder, J.H.6    Sharpless, B.K.7    Fokin, V.V.8
  • 55
    • 33745727392 scopus 로고    scopus 로고
    • Synthetic utility of glycosyl triazoles in carbohydrate chemistry
    • 1:CAS:528:DC%2BD28XmvFeltbk%3D 10.1016/j.tet.2006.06.001
    • BL Wilkinson LF Bornaghi S-A Poulsen TA Houston 2006 Synthetic utility of glycosyl triazoles in carbohydrate chemistry Tetrahedron 62 8115 8125 1:CAS:528:DC%2BD28XmvFeltbk%3D 10.1016/j.tet.2006.06.001
    • (2006) Tetrahedron , vol.62 , pp. 8115-8125
    • Wilkinson, B.L.1    Bornaghi, L.F.2    Poulsen, S.-A.3    Houston, T.A.4
  • 56
    • 2542511752 scopus 로고    scopus 로고
    • Highly efficient enantiospecific synthesis of imidazoline-containing amino acids using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate
    • 1:CAS:528:DC%2BD2cXjt1Ggs78%3D 10.1021/ol049439c 15128266
    • SL You JF Kelly 2004 Highly efficient enantiospecific synthesis of imidazoline-containing amino acids using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate Org Lett 6 1681 1683 1:CAS:528:DC%2BD2cXjt1Ggs78%3D 10.1021/ol049439c 15128266
    • (2004) Org Lett , vol.6 , pp. 1681-1683
    • You, S.L.1    Kelly, J.F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.