Modellsynthesen von Oligo- und Polynucleotiden

Kricheldorf, Hans R.

doi:10.1007/978-3-662-57978-7_7

Hans R. Kricheldorf²

1635 Accesses

Zusammenfassung

Die ersten Untersuchungen zur präbiotischen Bildung von Poly(ribonucleotiden) wurden schon kurz vor 1960 veröffentlicht. A. M. Michelson polymerisierte die 2′,3′-Zyklophosphate aller vier Nucleoside mithilfe von Phenylphosphorochloridat und erhielt Gemische von 2′,5′- und 3′,5′-verknüpften Nucleosidpolyphosphaten. Dieser Autor beschrieb auch eine schrittweise Synthese bis hin zu einem DP 6. Khorana und Mitarbeiter verwendeten Dicyclohexylcarbodiimid als Kondensationsmittel und umgingen die Problematik der unerwünschten Verknüpfung der 2′-OH-Gruppe zunächst dadurch, dass mit Thymidylsäure ein Deoxyribonucleosid eingesetzt wurde.

Es erfordert mehr Mut seine Ansicht zu ändern, als an ihr festzuhalten.

(Norrisat Perseshkian)

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Chapter: USD 29.95; Price excludes VAT (USA)

eBook: USD 59.99; Price excludes VAT (USA)

Softcover Book: USD 74.99; Price excludes VAT (USA)

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Literatur

Adamale K, Engelhart AE, Sczostak JW (2015) J Am Chem Soc 137:483
Article CAS Google Scholar
Blain JC, Ricardo A, Sczosttak JW (2014) J Am Chem Soc 136:2033
Article CAS PubMed PubMed Central Google Scholar
Bowler FR, Chan CKW, Duffy CD, Gerland B, Islam S, Powner FR, Sutherland JD (2013) Nat Chem 5:383
Article CAS PubMed PubMed Central Google Scholar
Bridson PK, Orgel LE (1980) J Mol Biol 144:567–577
Article CAS PubMed Google Scholar
Coutsogeorgopoulos C, Khorana AG (1964) J Am Chem Soc 86:2920
Article Google Scholar
Cramer F (1961) Angew Chem 1961(73):49
Article Google Scholar
Dolinnaya NG, Sokolova NI, Gryaznova OI, Shabarova ZA (1988) Nucleic Acids Res 16:3721
Article CAS PubMed PubMed Central Google Scholar
Dolinnaya NG, Sokolova NI, Ashirbekova DT, Shabarova ZA (1991) Nucleic Acids Res 11:3067
Article Google Scholar
Engelhart AE, Powner MW, Sczostak JW (2013) Nature 5:390
CAS Google Scholar
Ertem G, Ferris JP (1996) Nature 379:238
Article CAS PubMed Google Scholar
Fahrenbach AC, Giurgiu C, Tam CP, Li L, Hongo Y, Aono YM, Sczostak JW (2017) J Am Chem Soc 139:8780
Article CAS PubMed PubMed Central Google Scholar
Fakrai H, VanRoode JHG, Orgel LE (1981) J Mol Evol 17:295–302
Article Google Scholar
Ferris JP, Huand CH, Hagan WJ (1989a) Nucleosides Nucleotides 8(3):407
Article CAS PubMed Google Scholar
Ferris JP, Ertem G (1992) 257:1387
Google Scholar
Ferris JP, Ertem G (1993) J Am Chem Soc 115:12270
Article CAS PubMed Google Scholar
Ferris JP, Hill AR Jr, Liu R, Orgel LE (1996) Nature 381:59
Article CAS PubMed Google Scholar
Gao K, Orgel LE (2000) Orig Life Evol Biosph 30:45
Article CAS PubMed Google Scholar
Gibbs D, Lohrmann R, Orgel LE (1980) J Mol Evol 1980(15):347–357
Article Google Scholar
Gilham PT, Khorana HG (1958) J Am Chem Soc 80:6212
Article CAS Google Scholar
Giurgiu C, Li L, O’Flaherty DK, Tam CP, Sczostak JW (2017) J Am Chem Soc 139:16741
Google Scholar
Harada K, Orgel LE (1994) J Mol Biol 38:558
CAS Google Scholar
Hayes FN, Hansbury E (1964) J Am Chem Soc 86:4172
Article CAS Google Scholar
Hill AR Jr, Kumar S, Patil VD, Leonard NJ, Orgel LE (1991) J Mol Evol 32:447
Article CAS PubMed Google Scholar
Horowitz ED, Engelhart AE, Chen MC, Quales KA, Smith MW, Lynn DG, Hud NV (2010) Proc Acad Natl Sci USA 107:5288
Article CAS Google Scholar
Huang W, Ferris JP (2003) Chem Commun, 1458
Google Scholar
Hulshof J, Ponnamperuma C (1976) Origins Life 7:197
Article CAS PubMed Google Scholar
Ibanez JD, Kimball AP, Oro J (1971) Science 173:444–446
Article CAS PubMed Google Scholar
Inoue T, Orgel LE (1982) J Mol Evol 162:201–217
CAS Google Scholar
Izgu EC, Oh SS, Sczostak JW (2016) Chem Commun 52:3684
Article CAS Google Scholar
Jia TZ, Fahrenbach AC, Kanat KP, Adamale KP, Sczostak JW (2016) Nat Chem 8:915
Article CAS PubMed PubMed Central Google Scholar
Jia TZ, Fahrenbach AC, Kanat NP, Adamale KP, Sczostak JW (2017) Nat Chem 9:1286
Article CAS PubMed PubMed Central Google Scholar
Joyce GF, Orgel LE (1986) J Mol Biol 188:433–441
Article CAS PubMed Google Scholar
Joyce GF, Orgel LE (1988) J Mol Biol 202:677–681
Article CAS PubMed Google Scholar
Joyce GF, Visser GM, Van Bockelt CAA, van Boom JH, Orgel LE, van Vestrem J (1984a) J Nat 310:602–604
Article CAS Google Scholar
Joyce GF, Inoue T, Orgel LE (1984b) J Mol Biol 176:279–300
Article CAS PubMed Google Scholar
Kanya E, Yanagawa H (1986) Biochemistry 25:7423–7430
Article Google Scholar
Khorana HG, Tener GM, Moffat JG, Pol RM (1956) Chem Ind 1523
Google Scholar
Khorana HG, Razzeli WE, Gilham P, Tenner GM, Pol RM (1957) J Am Chem Soc 79:1002
Article CAS Google Scholar
Kozlov IA, Orgel LE (2000) Mol Biol 34:781–789
Article CAS Google Scholar
Kozlov IA, Pitsch S, Orgel LE (1998) Proc Natl Acad Sci 95:13448
Article CAS PubMed PubMed Central Google Scholar
Li L, Prywes N, Tam CP, O’Flaherty DK, Lilyveld VS, Izgu EC, Pal A, Sczostak JW (2017) J Am Chem Soc 139:1810
Google Scholar
Lohrmann R, Orgel LE (1977) J Mol Biol 119:193
Article Google Scholar
Lohrmann R, Orgel LE (1979a) J Mol Evol 12:237–257
Article CAS PubMed Google Scholar
Lohrmann R, Orgel LE (1979b) J Mol Evol 14:243
Article CAS PubMed Google Scholar
Lohrmann R, Orgel LE (1980) J Mol Biol 142:555–567
Article CAS PubMed Google Scholar
Lohrmann R, Bridson PK, Orgel LE (1981) J Mol Evol 17:303–306
Article CAS PubMed Google Scholar
Lohrmann R (1982) J Mol Evol 1982(18):185–195
Article Google Scholar
Michelson AM (1959) J Chem Soc (London) 1371:3655
Google Scholar
Nagyvary J, Nagpal KL (1972) Science 177:272
Article CAS PubMed Google Scholar
Naylor R, Gilham PT (1966) Biochemistry 5:3722
Article Google Scholar
Nig KME, Orgel LE (1989) J Mol Evol 29:101
Article Google Scholar
Ninio J, Orgel LE (1978) J Mol Evol 12:91
Article CAS PubMed Google Scholar
Orgel LE, Lohrmann R (1974) Acc Chem Res 7:365
Article Google Scholar
Pal A, Das RS, Zhang W, Lang M, Mclaughlin MW, Larry W, Sczostak JW (2016) Chem Commun 52:11905
Article CAS Google Scholar
Powner MW, Gerland B, Sutherland JD (2009) Nature 459:239
Article CAS PubMed Google Scholar
Prabahr KJ, Ferris JP (1997) J Am Chem Soc 119:4330
Article Google Scholar
Rembold HJ, Orgel LE (1994) J Mol Evol 38:205
CAS PubMed Google Scholar
Renz M, Lohrmann R, Orgel LE (1971) Biochim Biophys Acta 240:463–471
Article CAS PubMed Google Scholar
Rodriguez L, Orgel LE (1991) J Mol Evol 191(33):477
Article Google Scholar
Rohatgi R, Bartel DP, Sczostak JW (1996a) J Am Chem Soc 118:3332
Article CAS PubMed Google Scholar
Rohatgi R, Bartel DP, Sczostak JW (1996b) J Am Chem Soc 118:3340
Article CAS PubMed Google Scholar
Sawai H (1976) J Am Chem Soc 98:7037
Article CAS PubMed Google Scholar
Sawai H, Orgel LE (1975) J Am Chem Soc 97:3532
Article CAS PubMed Google Scholar
Sawai H, Shibata T, Ono M (1981) Tetrahedron 37:481
Article CAS Google Scholar
Sawai H, Kuroda K, Hojo T (1989) Bull Chem Soc Japan 62:2018
Article CAS Google Scholar
Schneider-Bernloehr H, Lohrman R, Sulston J, Weimann BJ, Orgel LE (1968) J Mol Biol 37:131
Article Google Scholar
Schramm G (1965) In: Fox SW (Hrsg) The origin of prebiological systems. Academic Press, New York, S 299
Google Scholar
Schramm G, Grötsch H, Pollmann W (1961) Angew Chem 73:619
Article CAS Google Scholar
Schramm G, Grötsch H, Pollmann W (1962) Angew Chem Int Ed 1:1
Article Google Scholar
Schrum JP, Ricardo A, Krishnamurthy M, Blain JC, Sczostak JW (2009) J Am Chem Soc 131:14560
Article CAS PubMed PubMed Central Google Scholar
Schwartz AW, Bradley E, Fox SW (1965) In: Fox SW (Hrsg) The origin of prebiological systems. Academic Press, New York, S 317
Google Scholar
Shapiro R (2006) Quart Rev Biol 81:105
Article PubMed Google Scholar
Sleeper HL, Orgel LE (1979) J Mol Evol 12:357
Article CAS PubMed Google Scholar
Sulston J, Lohrmann R, Orgel LE, Miles HT (1968a) Proc Natl Acad Sci USA 59:409, 726
Google Scholar
Sulston J, Lohrmann R, Orgel LE, Miles HT (1968b) Science 60:409
CAS Google Scholar
Tam CP, Zhu L, Fahrenbach AC, Zhang W, Walton T, Sczostak JW (2017) J Am Chem Soc 140:783
Article PubMed Central CAS Google Scholar
Tener GM, Khorana HG, Markham R, Pol EH (1958) J Am Chem Soc 80:6223
Article CAS Google Scholar
Toiichi M, Zielinski WS, Chen CHB, Orgel LE (1987) J Mol Evol 25:97
Article Google Scholar
Uesugi S, Tso POP (1974) Biochemistry 13:3142
Article CAS PubMed Google Scholar
Usher DA, Mc Hale AH (1976) Science 192:53
Article CAS PubMed Google Scholar
VanRoode JHG, Orgel LE (1980) J Mol Biol 144:579
Article CAS Google Scholar
Verlander MS, Lohrmann R, Orgel LE (1973) J Mol Evol 2:303–316
Article CAS PubMed Google Scholar
Verlander MS, Orgel LE (1974) J Mol Evol 3:115–120
Article CAS PubMed Google Scholar
Visscher J, Bakker CG, van der Woerd R, Schwartz AW (1989) Science 244:4902
Article Google Scholar
Walton WT, Sczostak JW (2017) Biochemistry 56(57):39
Google Scholar
Weimann BJ, Orgel LE, Schneider-Bernloehr H, Sulston JE (1968) Science 161:387
Article CAS PubMed Google Scholar
Zielinski WS, Orgel LE (1987a) Nature 327:346
Article CAS PubMed Google Scholar
Zhang N, Zhang S, Sczostak JW (2012) J Am Chem Soc 134:3691
Article CAS PubMed PubMed Central Google Scholar
Zhang S, Blain JC, Zielinska D, Gyraznov SM, Jostak JW (2013a) Proc Natl Acad Sci USA 110:17732
Article CAS PubMed PubMed Central Google Scholar
Zhang N, Zhang S, Blain JC, Sczostal JW (2013b) J Am Chem Soc 135:924
Article CAS PubMed Google Scholar
Zhang W, Tam CP, Walton WT, Fahrenbach AC, Birrane G, Sczostak JW (2017) Proc Natl Acad Sci USA 114:7659
Article CAS PubMed PubMed Central Google Scholar
Zielinski WS, Orgel LE (1987b) Nature 327:127
Article Google Scholar

Weiterführende Literatur

Ferris JP, Huang CH, Hagan WJ (1989b) Nuceosides and Nucleotides 8:407–414
Article CAS Google Scholar
Hill AR, Orgel LE, Robins RK (1988) J Mol Evol 28:170–171
Article CAS PubMed Google Scholar
Hill AR, Kumar S, Patil VD, Leonard NJ, Rembold H, Orgel LE (1994) J Mol Evol 38:205–210
Google Scholar
Inoue T, Joyce GF, Greskoviak K, Orgel LE (1984) 178:669–676
Google Scholar
Kolb V, Orgel LE (1995) J Mol Evol 1995(40):115–119
Article Google Scholar
Lohrmann R, Orgel LE (1978) Tetrahedron 34:853–255
Article CAS Google Scholar
Mansy SS, Schrum JP, Krishnamurthy M, Tobe S, Treco DA, Szostak JW (2008) Nature 454:122
Article CAS PubMed PubMed Central Google Scholar
Xu J (2013) Nat Chem 5:383
Article PubMed PubMed Central CAS Google Scholar

Download references

Author information

Authors and Affiliations

Institute for Technical and Makromolekular Chemistry, Universität Hamburg, Hamburg, Deutschland
Hans R. Kricheldorf

Authors

Hans R. Kricheldorf
View author publications
You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hans R. Kricheldorf .

Rights and permissions

Reprints and permissions

Copyright information

About this chapter

Cite this chapter

Kricheldorf, H. (2019). Modellsynthesen von Oligo- und Polynucleotiden. In: Leben durch chemische Evolution?. Springer Spektrum, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-57978-7_7

Download citation

DOI: https://doi.org/10.1007/978-3-662-57978-7_7
Published: 07 June 2019
Publisher Name: Springer Spektrum, Berlin, Heidelberg
Print ISBN: 978-3-662-57977-0
Online ISBN: 978-3-662-57978-7
eBook Packages: Life Science and Basic Disciplines (German Language)

Publish with us

Policies and ethics