Water-Soluble Supramolecular Polymers of Paired and Stacked Heterocycles: Assembly, Structure, Properties, and a Possible Path to Pre-RNA
The hypothesis that RNA and DNA are products of chemical and biological evolution has motivated our search for alternative nucleic acids that may have come earlier in the emergence of lifepolymers that possess a proclivity for covalent and non-covalent self-assembly not exhibited by RNA. Our invest...
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Published in | Journal of the American Chemical Society Vol. 143; no. 25; pp. 9279 - 9296 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
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United States
American Chemical Society
30.06.2021
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Abstract | The hypothesis that RNA and DNA are products of chemical and biological evolution has motivated our search for alternative nucleic acids that may have come earlier in the emergence of lifepolymers that possess a proclivity for covalent and non-covalent self-assembly not exhibited by RNA. Our investigations have revealed a small set of candidate ancestral nucleobases that self-assemble into hexameric rosettes that stack in water to form long, twisted, rigid supramolecular polymers. These structures exhibit properties that provide robust solutions to long-standing problems that have stymied the search for a prebiotic synthesis of nucleic acids. Moreover, their examination by experimental and computational methods provides insight into the chemical and physical principles that govern a particular class of water-soluble one-dimensional supramolecular polymers. In addition to efficient self-assembly, their lengths and polydispersity are modulated by a wide variety of positively charged, planar compounds; their assembly and disassembly are controlled over an exceedingly narrow pH range; they exhibit spontaneous breaking of symmetry; and homochirality emerges through non-covalent cross-linking during hydrogel formation. Some of these candidate ancestral nucleobases spontaneously form glycosidic bonds with ribose and other sugars, and, most significantly, functionalized forms of these heterocycles form supramolecular structures and covalent polymers under plausibly prebiotic conditions. This Perspective recounts a journey of discovery that continues to reveal attractive answers to questions concerning the origins of life and to uncover the principles that control the structure and properties of water-soluble supramolecular polymers. |
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AbstractList | The hypothesis that RNA and DNA are products of chemical and biological evolution has motivated our search for alternative nucleic acids that may have come earlier in the emergence of lifepolymers that possess a proclivity for covalent and non-covalent self-assembly not exhibited by RNA. Our investigations have revealed a small set of candidate ancestral nucleobases that self-assemble into hexameric rosettes that stack in water to form long, twisted, rigid supramolecular polymers. These structures exhibit properties that provide robust solutions to long-standing problems that have stymied the search for a prebiotic synthesis of nucleic acids. Moreover, their examination by experimental and computational methods provides insight into the chemical and physical principles that govern a particular class of water-soluble one-dimensional supramolecular polymers. In addition to efficient self-assembly, their lengths and polydispersity are modulated by a wide variety of positively charged, planar compounds; their assembly and disassembly are controlled over an exceedingly narrow pH range; they exhibit spontaneous breaking of symmetry; and homochirality emerges through non-covalent cross-linking during hydrogel formation. Some of these candidate ancestral nucleobases spontaneously form glycosidic bonds with ribose and other sugars, and, most significantly, functionalized forms of these heterocycles form supramolecular structures and covalent polymers under plausibly prebiotic conditions. This Perspective recounts a journey of discovery that continues to reveal attractive answers to questions concerning the origins of life and to uncover the principles that control the structure and properties of water-soluble supramolecular polymers. The hypothesis that RNA and DNA are products of chemical and biological evolution has motivated our search for alternative nucleic acids that may have come earlier in the emergence of life-polymers that possess a proclivity for covalent and non-covalent self-assembly not exhibited by RNA. Our investigations have revealed a small set of candidate ancestral nucleobases that self-assemble into hexameric rosettes that stack in water to form long, twisted, rigid supramolecular polymers. These structures exhibit properties that provide robust solutions to long-standing problems that have stymied the search for a prebiotic synthesis of nucleic acids. Moreover, their examination by experimental and computational methods provides insight into the chemical and physical principles that govern a particular class of water-soluble one-dimensional supramolecular polymers. In addition to efficient self-assembly, their lengths and polydispersity are modulated by a wide variety of positively charged, planar compounds; their assembly and disassembly are controlled over an exceedingly narrow pH range; they exhibit spontaneous breaking of symmetry; and homochirality emerges through non-covalent cross-linking during hydrogel formation. Some of these candidate ancestral nucleobases spontaneously form glycosidic bonds with ribose and other sugars, and, most significantly, functionalized forms of these heterocycles form supramolecular structures and covalent polymers under plausibly prebiotic conditions. This Perspective recounts a journey of discovery that continues to reveal attractive answers to questions concerning the origins of life and to uncover the principles that control the structure and properties of water-soluble supramolecular polymers. |
Author | Hud, Nicholas V Karunakaran, Suneesh C Schuster, Gary B Cafferty, Brian J |
AuthorAffiliation | School of Chemistry and Biochemistry NSF-NASA Center for Chemical Evolution |
AuthorAffiliation_xml | – name: NSF-NASA Center for Chemical Evolution – name: School of Chemistry and Biochemistry |
Author_xml | – sequence: 1 givenname: Gary B surname: Schuster fullname: Schuster, Gary B – sequence: 2 givenname: Brian J surname: Cafferty fullname: Cafferty, Brian J – sequence: 3 givenname: Suneesh C orcidid: 0000-0002-9587-4645 surname: Karunakaran fullname: Karunakaran, Suneesh C – sequence: 4 givenname: Nicholas V orcidid: 0000-0001-7711-6472 surname: Hud fullname: Hud, Nicholas V email: hud@chemistry.gatech.edu |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/34152760$$D View this record in MEDLINE/PubMed |
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Cites_doi | 10.1073/pnas.1311778111 10.1007/s00239-015-9669-9 10.1002/hlca.19920750503 10.1021/ja104387k 10.1021/jacs.0c03353 10.1002/anie.200300589 10.1016/0371-1951(64)80037-0 10.1021/acsomega.7b02039 10.1002/marc.201400623 10.1021/la201415d 10.1038/nmat2614 10.1021/ja047783z 10.1021/ja801804c 10.1021/acs.chemrev.5b00369 10.1021/cr500671p 10.1080/07391102.1990.10507825 10.1023/A:1020139302770 10.1021/ja5035107 10.1021/jp709613p 10.1021/ja105028w 10.1002/chem.200902415 10.1002/anie.201303810 10.1038/nchem.2075 10.1101/cshperspect.a002196 10.1007/s11084-005-5945-9 10.1089/ast.2014.1264 10.1039/C6CP04230A 10.1038/ncomms6793 10.1002/anie.201812808 10.1002/chem.201204313 10.1016/0008-6215(94)84109-8 10.1039/C4SC02182G 10.1038/nmat3776 10.1016/j.cbpa.2014.09.015 10.1073/pnas.1009592107 10.1126/science.161.3839.387 10.1246/bcsj.81.1196 10.1021/ja00027a040 10.1038/nchem.2628 10.1063/1.2409296 10.1002/anie.201707392 10.1021/jacs.9b09443 10.1016/j.bbrc.2011.09.008 10.1186/1745-6150-7-23 10.1002/anie.201902050 10.1007/BF01660244 10.1038/s41586-020-2330-9 10.1002/chem.19970030715 10.3390/sym12121982 10.1039/b305550g 10.1021/j100009a052 10.1007/s11084-013-9334-5 10.1016/0022-2836(68)90393-8 10.3390/life10120346 10.1002/cbic.201000074 10.1038/nchem.1241 10.1039/C6CC08226B 10.1007/s11084-011-9249-y 10.1016/0022-2836(72)90383-X 10.1021/ja981554t 10.1073/pnas.111158498 10.1073/pnas.1106493108 10.1021/ja00089a021 10.1016/j.addr.2006.09.020 10.1126/science.268.5219.1860 10.1063/1.476623 10.1021/ja00892a016 10.1039/b511984g 10.1080/10409230490460765 10.1021/ar00049a006 10.1055/s-0030-1261177 10.1093/nar/gkz496 10.1039/C6CS00183A 10.1126/science.aax2747 10.1107/S0567740871005880 10.1039/C5CC10317G 10.1073/pnas.48.12.2013 10.1089/ast.2011.0726 10.1016/S0040-6090(96)09066-9 10.1021/ja806524m 10.1016/j.chembiol.2013.03.012 10.1039/b503463a 10.1002/anie.199500581 10.1002/anie.200603207 10.1002/chem.201706070 10.1021/acsami.7b00957 10.1021/la9817157 10.1021/ja00039a096 10.1021/jacs.0c12010 10.1016/S0968-0004(98)01300-0 10.1021/ma0518914 10.1038/nature04162 10.1021/ja036465h 10.3390/molecules21121645 10.1103/PhysRevB.40.5140 10.1021/ar040004z 10.1006/jtbi.2000.2084 10.3390/life9010017 10.1038/ncomms11328 10.1007/978-3-319-93584-3_5 10.1007/s11084-017-9532-7 10.1126/science.1217622 10.1021/bi00338a008 10.1039/a606340c 10.1007/s11426-009-0115-y 10.1021/ja410124v 10.1039/C6CC04427A 10.1002/cbdv.200790063 10.1021/ma60008a005 10.1002/chem.201600478 10.1126/science.284.5423.2118 10.1039/p29920000461 10.1021/bi025551b 10.1088/0953-8984/2/33/001 10.1016/0022-2836(68)90392-6 10.1039/c39900000479 10.1039/b101678b 10.1021/bk-2009-1025.ch007 10.1038/35025027 10.1073/pnas.032527099 10.1039/C6CP00686H 10.1351/pac199870020263 10.1073/pnas.1721369115 10.1039/C8PY01146J 10.1038/381059a0 10.1002/bies.201000058 10.1002/cphc.201500601 10.1002/chem.200802656 10.1016/S1074-5521(97)90298-2 10.1103/PhysRevLett.76.58 10.1016/S0040-4020(01)99315-9 10.1021/ja900807m 10.1021/jacs.7b01562 10.1021/ja00089a022 10.1039/c39930001382 10.1021/ja312155v 10.1021/acs.accounts.6b00594 10.1021/jo4019792 10.1021/bi992070s 10.1039/c1cc11178g 10.1002/cbic.202000510 10.1021/ja005886l 10.1007/s00114-005-0073-y 10.1021/ja211113n 10.1002/chem.201102435 10.1002/(SICI)1521-3765(19990104)5:1<381::AID-CHEM381>3.0.CO;2-T 10.1002/pola.28954 10.1126/science.aad2808 10.1002/masy.19940770119 10.1002/anie.199710061 10.1002/anie.201609252 10.1021/ja00173a046 10.1002/anie.199622041 10.1016/S0968-0896(00)00340-0 10.1002/1521-3765(20020301)8:5<1227::AID-CHEM1227>3.0.CO;2-0 |
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References | ref99/cit99 ref3/cit3 ref81/cit81 ref16/cit16 ref52/cit52 ref114/cit114 ref23/cit23 ref115/cit115 ref116/cit116 ref110/cit110 ref111/cit111 ref2/cit2 ref112/cit112 ref77/cit77 ref113/cit113 ref71/cit71 ref117/cit117 ref20/cit20 ref48/cit48 ref118/cit118 ref74/cit74 ref119/cit119 ref10/cit10 ref35/cit35 ref89/cit89 ref19/cit19 ref93/cit93 ref42/cit42 ref96/cit96 ref107/cit107 ref120/cit120 ref109/cit109 ref13/cit13 ref122/cit122 ref105/cit105 ref61/cit61 ref67/cit67 ref38/cit38 ref90/cit90 ref124/cit124 ref64/cit64 ref126/cit126 ref54/cit54 ref6/cit6 ref18/cit18 ref136/cit136 ref137/cit137 ref65/cit65 ref97/cit97 ref101/cit101 ref11/cit11 ref102/cit102 ref29/cit29 ref76/cit76 ref86/cit86 ref32/cit32 ref39/cit39 ref5/cit5 ref43/cit43 ref80/cit80 ref133/cit133 ref28/cit28 ref132/cit132 ref91/cit91 ref148/cit148 ref55/cit55 ref144/cit144 ref12/cit12 ref66/cit66 ref22/cit22 ref121/cit121 ref33/cit33 ref87/cit87 ref106/cit106 ref140/cit140 ref129/cit129 ref44/cit44 ref70/cit70 ref98/cit98 ref125/cit125 ref9/cit9 ref152/cit152 ref153/cit153 ref154/cit154 ref27/cit27 ref150/cit150 ref63/cit63 ref151/cit151 ref56/cit56 ref159/cit159 ref92/cit92 ref155/cit155 ref156/cit156 ref157/cit157 ref158/cit158 ref8/cit8 ref31/cit31 ref59/cit59 ref85/cit85 ref34/cit34 ref37/cit37 ref60/cit60 ref88/cit88 ref17/cit17 ref82/cit82 ref147/cit147 ref160/cit160 ref143/cit143 Bang I. (ref45/cit45) 1910; 26 ref53/cit53 ref145/cit145 ref21/cit21 ref149/cit149 ref46/cit46 ref49/cit49 ref75/cit75 ref24/cit24 ref141/cit141 ref50/cit50 ref78/cit78 ref36/cit36 ref83/cit83 ref138/cit138 ref79/cit79 ref139/cit139 ref100/cit100 ref25/cit25 ref103/cit103 ref72/cit72 ref14/cit14 ref57/cit57 ref51/cit51 ref134/cit134 ref135/cit135 ref40/cit40 ref68/cit68 ref94/cit94 ref130/cit130 ref131/cit131 ref146/cit146 ref26/cit26 ref142/cit142 ref73/cit73 ref69/cit69 Yoshioka D. (ref128/cit128) 2007 ref15/cit15 ref62/cit62 ref41/cit41 ref58/cit58 ref95/cit95 ref108/cit108 ref4/cit4 ref30/cit30 ref47/cit47 ref84/cit84 ref127/cit127 ref1/cit1 ref123/cit123 ref7/cit7 |
References_xml | – ident: ref32/cit32 doi: 10.1073/pnas.1311778111 – ident: ref24/cit24 doi: 10.1007/s00239-015-9669-9 – ident: ref25/cit25 doi: 10.1002/hlca.19920750503 – ident: ref108/cit108 doi: 10.1021/ja104387k – ident: ref109/cit109 doi: 10.1021/jacs.0c03353 – ident: ref47/cit47 doi: 10.1002/anie.200300589 – ident: ref79/cit79 doi: 10.1016/0371-1951(64)80037-0 – ident: ref49/cit49 doi: 10.1021/acsomega.7b02039 – ident: ref130/cit130 doi: 10.1002/marc.201400623 – ident: ref97/cit97 doi: 10.1021/la201415d – ident: ref139/cit139 doi: 10.1038/nmat2614 – ident: ref96/cit96 doi: 10.1021/ja047783z – ident: ref106/cit106 doi: 10.1021/ja801804c – volume: 26 start-page: 293 year: 1910 ident: ref45/cit45 publication-title: Biochem. Z. contributor: fullname: Bang I. – ident: ref100/cit100 doi: 10.1021/acs.chemrev.5b00369 – ident: ref151/cit151 doi: 10.1021/cr500671p – ident: ref46/cit46 doi: 10.1080/07391102.1990.10507825 – ident: ref71/cit71 doi: 10.1023/A:1020139302770 – ident: ref110/cit110 doi: 10.1021/ja5035107 – ident: ref137/cit137 doi: 10.1021/jp709613p – ident: ref51/cit51 doi: 10.1021/ja105028w – ident: ref115/cit115 doi: 10.1002/chem.200902415 – ident: ref132/cit132 doi: 10.1002/anie.201303810 – ident: ref55/cit55 doi: 10.1038/nchem.2075 – ident: ref21/cit21 doi: 10.1101/cshperspect.a002196 – ident: ref76/cit76 doi: 10.1007/s11084-005-5945-9 – ident: ref64/cit64 doi: 10.1089/ast.2014.1264 – ident: ref81/cit81 doi: 10.1039/C6CP04230A – ident: ref54/cit54 doi: 10.1038/ncomms6793 – ident: ref113/cit113 doi: 10.1002/anie.201812808 – ident: ref72/cit72 doi: 10.1002/chem.201204313 – ident: ref67/cit67 doi: 10.1016/0008-6215(94)84109-8 – ident: ref133/cit133 doi: 10.1039/C4SC02182G – ident: ref142/cit142 doi: 10.1038/nmat3776 – ident: ref23/cit23 doi: 10.1016/j.cbpa.2014.09.015 – ident: ref102/cit102 doi: 10.1073/pnas.1009592107 – ident: ref17/cit17 doi: 10.1126/science.161.3839.387 – ident: ref154/cit154 doi: 10.1246/bcsj.81.1196 – ident: ref18/cit18 doi: 10.1021/ja00027a040 – ident: ref159/cit159 doi: 10.1038/nchem.2628 – ident: ref121/cit121 doi: 10.1063/1.2409296 – ident: ref155/cit155 doi: 10.1002/anie.201707392 – ident: ref129/cit129 doi: 10.1021/jacs.9b09443 – ident: ref13/cit13 doi: 10.1016/j.bbrc.2011.09.008 – ident: ref2/cit2 – ident: ref22/cit22 doi: 10.1186/1745-6150-7-23 – ident: ref19/cit19 doi: 10.1002/anie.201902050 – ident: ref69/cit69 doi: 10.1007/BF01660244 – ident: ref10/cit10 doi: 10.1038/s41586-020-2330-9 – ident: ref86/cit86 doi: 10.1002/chem.19970030715 – ident: ref145/cit145 doi: 10.3390/sym12121982 – ident: ref150/cit150 doi: 10.1039/b305550g – ident: ref39/cit39 doi: 10.1021/j100009a052 – ident: ref15/cit15 doi: 10.1007/s11084-013-9334-5 – ident: ref4/cit4 doi: 10.1016/0022-2836(68)90393-8 – ident: ref33/cit33 doi: 10.3390/life10120346 – ident: ref74/cit74 doi: 10.1002/cbic.201000074 – ident: ref30/cit30 doi: 10.1038/nchem.1241 – ident: ref149/cit149 doi: 10.1039/C6CC08226B – ident: ref14/cit14 doi: 10.1007/s11084-011-9249-y – ident: ref68/cit68 doi: 10.1016/0022-2836(72)90383-X – ident: ref126/cit126 doi: 10.1021/ja981554t – ident: ref40/cit40 doi: 10.1073/pnas.111158498 – ident: ref70/cit70 doi: 10.1073/pnas.1106493108 – ident: ref93/cit93 doi: 10.1021/ja00089a021 – ident: ref138/cit138 doi: 10.1016/j.addr.2006.09.020 – ident: ref157/cit157 doi: 10.1126/science.268.5219.1860 – ident: ref1/cit1 – ident: ref119/cit119 doi: 10.1063/1.476623 – ident: ref43/cit43 doi: 10.1021/ja00892a016 – ident: ref95/cit95 doi: 10.1039/b511984g – ident: ref5/cit5 doi: 10.1080/10409230490460765 – ident: ref90/cit90 doi: 10.1021/ar00049a006 – ident: ref6/cit6 doi: 10.1055/s-0030-1261177 – ident: ref160/cit160 doi: 10.1093/nar/gkz496 – ident: ref48/cit48 doi: 10.1039/C6CS00183A – ident: ref9/cit9 doi: 10.1126/science.aax2747 – ident: ref98/cit98 doi: 10.1107/S0567740871005880 – ident: ref61/cit61 doi: 10.1039/C5CC10317G – ident: ref99/cit99 doi: 10.1073/pnas.48.12.2013 – ident: ref73/cit73 doi: 10.1089/ast.2011.0726 – ident: ref89/cit89 doi: 10.1016/S0040-6090(96)09066-9 – ident: ref111/cit111 doi: 10.1021/ja806524m – ident: ref35/cit35 doi: 10.1016/j.chembiol.2013.03.012 – ident: ref123/cit123 doi: 10.1039/b503463a – ident: ref62/cit62 doi: 10.1002/anie.199500581 – ident: ref29/cit29 doi: 10.1002/anie.200603207 – ident: ref153/cit153 doi: 10.1002/chem.201706070 – ident: ref141/cit141 doi: 10.1021/acsami.7b00957 – ident: ref103/cit103 doi: 10.1021/la9817157 – ident: ref85/cit85 doi: 10.1021/ja00039a096 – ident: ref112/cit112 doi: 10.1021/jacs.0c12010 – ident: ref57/cit57 doi: 10.1016/S0968-0004(98)01300-0 – ident: ref122/cit122 doi: 10.1021/ma0518914 – ident: ref41/cit41 doi: 10.1038/nature04162 – ident: ref12/cit12 doi: 10.1021/ja036465h – ident: ref80/cit80 doi: 10.3390/molecules21121645 – ident: ref116/cit116 doi: 10.1103/PhysRevB.40.5140 – ident: ref28/cit28 doi: 10.1021/ar040004z – ident: ref34/cit34 doi: 10.1006/jtbi.2000.2084 – ident: ref58/cit58 doi: 10.3390/life9010017 – ident: ref36/cit36 doi: 10.1038/ncomms11328 – ident: ref37/cit37 doi: 10.1007/978-3-319-93584-3_5 – ident: ref16/cit16 doi: 10.1007/s11084-017-9532-7 – ident: ref31/cit31 doi: 10.1126/science.1217622 – ident: ref107/cit107 doi: 10.1021/bi00338a008 – ident: ref87/cit87 doi: 10.1039/a606340c – ident: ref146/cit146 doi: 10.1007/s11426-009-0115-y – ident: ref65/cit65 doi: 10.1021/ja410124v – ident: ref148/cit148 doi: 10.1039/C6CC04427A – ident: ref56/cit56 doi: 10.1002/cbdv.200790063 – ident: ref118/cit118 doi: 10.1021/ma60008a005 – ident: ref120/cit120 doi: 10.1002/chem.201600478 – ident: ref27/cit27 doi: 10.1126/science.284.5423.2118 – ident: ref84/cit84 doi: 10.1039/p29920000461 – ident: ref105/cit105 doi: 10.1021/bi025551b – ident: ref117/cit117 doi: 10.1088/0953-8984/2/33/001 – ident: ref3/cit3 doi: 10.1016/0022-2836(68)90392-6 – volume-title: Statistical Physics: An Introduction year: 2007 ident: ref128/cit128 contributor: fullname: Yoshioka D. – ident: ref83/cit83 doi: 10.1039/c39900000479 – ident: ref125/cit125 doi: 10.1039/b101678b – ident: ref143/cit143 doi: 10.1021/bk-2009-1025.ch007 – ident: ref53/cit53 doi: 10.1038/35025027 – ident: ref101/cit101 doi: 10.1073/pnas.032527099 – ident: ref158/cit158 doi: 10.1039/C6CP00686H – ident: ref26/cit26 doi: 10.1351/pac199870020263 – ident: ref44/cit44 doi: 10.1073/pnas.1721369115 – ident: ref114/cit114 doi: 10.1039/C8PY01146J – ident: ref11/cit11 doi: 10.1038/381059a0 – ident: ref20/cit20 doi: 10.1002/bies.201000058 – ident: ref152/cit152 doi: 10.1002/cphc.201500601 – ident: ref59/cit59 doi: 10.1002/chem.200802656 – ident: ref63/cit63 doi: 10.1016/S1074-5521(97)90298-2 – ident: ref156/cit156 doi: 10.1103/PhysRevLett.76.58 – ident: ref78/cit78 doi: 10.1016/S0040-4020(01)99315-9 – ident: ref66/cit66 doi: 10.1021/ja900807m – ident: ref8/cit8 doi: 10.1021/jacs.7b01562 – ident: ref94/cit94 doi: 10.1021/ja00089a022 – ident: ref91/cit91 doi: 10.1039/c39930001382 – ident: ref38/cit38 doi: 10.1021/ja312155v – ident: ref42/cit42 doi: 10.1021/acs.accounts.6b00594 – ident: ref136/cit136 doi: 10.1021/jo4019792 – ident: ref127/cit127 doi: 10.1021/bi992070s – ident: ref147/cit147 doi: 10.1039/c1cc11178g – ident: ref60/cit60 doi: 10.1002/cbic.202000510 – ident: ref50/cit50 doi: 10.1021/ja005886l – ident: ref75/cit75 doi: 10.1007/s00114-005-0073-y – ident: ref140/cit140 doi: 10.1021/ja211113n – ident: ref131/cit131 doi: 10.1002/chem.201102435 – ident: ref135/cit135 doi: 10.1002/(SICI)1521-3765(19990104)5:1<381::AID-CHEM381>3.0.CO;2-T – ident: ref52/cit52 doi: 10.1002/pola.28954 – ident: ref7/cit7 doi: 10.1126/science.aad2808 – ident: ref92/cit92 doi: 10.1002/masy.19940770119 – ident: ref88/cit88 doi: 10.1002/anie.199710061 – ident: ref144/cit144 doi: 10.1002/anie.201609252 – ident: ref82/cit82 doi: 10.1021/ja00173a046 – ident: ref134/cit134 doi: 10.1002/anie.199622041 – ident: ref77/cit77 doi: 10.1016/S0968-0896(00)00340-0 – ident: ref124/cit124 doi: 10.1002/1521-3765(20020301)8:5<1227::AID-CHEM1227>3.0.CO;2-0 |
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Snippet | The hypothesis that RNA and DNA are products of chemical and biological evolution has motivated our search for alternative nucleic acids that may have come... |
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SubjectTerms | Evolution, Chemical Heterocyclic Compounds - chemistry Hydrogen Bonding Macromolecular Substances - chemistry Molecular Conformation Polymers - chemistry RNA - chemistry Solubility Water - chemistry |
Title | Water-Soluble Supramolecular Polymers of Paired and Stacked Heterocycles: Assembly, Structure, Properties, and a Possible Path to Pre-RNA |
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