Self-immolation Assisted Morphology Transformation of Prebiotic Lipidated-cationic Amino Acids: Electro-droplet Mediated C-C Coupling Reaction to Synthesize Macromolecules.
Origin of life
amino acid-based amphiphiles
compartmentalization
electrocatalysis
prebiotic macromolecules
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
15 Mar 2024
15 Mar 2024
Historique:
received:
27
10
2023
pubmed:
11
1
2024
medline:
11
1
2024
entrez:
11
1
2024
Statut:
ppublish
Résumé
Compartmentalization protected biomolecules from the fluctuating environments of early Earth. Although contemporary cells mostly use phospholipid-based bilayer membranes, the utility of non-bilayer compartments was not ruled out during the prebiotic and modern eras. In the present study, we demonstrated the prebiotic synthesis of lipidated cationic amino acid-based amphiphiles [lauryl ester of lysine (LysL); ornithine (OrnL); and 2,4-diamino butyric acid (DabL)] using model dry-down reaction. These amphiphiles self-assemble into micellar membranes. However, the OrnL and DabL-based micelles undergo pH-responsive transformation to lipid droplet-like morphologies, a modelcompartment in the prebiotic Earth. These cationic droplets encapsulated prebiotic molecules (isoprene) and assisted electron transfer reaction to synthesize isoprenoid derivatives at primitive Earth conditions. The self-assembly of prebiotic amphiphiles, their transformation to droplet compartments, and droplet-assisted C-C bond formation reaction might have helped the evolution to synthesize various biomolecules required for the origin of life.
Identifiants
pubmed: 38205907
doi: 10.1002/chem.202303555
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202303555Subventions
Organisme : SERB India
ID : CRG/2022/008554
Informations de copyright
© 2024 Wiley‐VCH GmbH.
Références
W. R. Hargreaves, D. W. Deamer, Biochemica 1978, 17, 3759–3768;
P. Walde, R. Wick, M. Fresta, A. Mangone, P. L. Luisi, J. Am. Chem. Soc. 1994, 116, 11649–11654;
J. W. Szostak, D. P. Bartel, P. L. Luisi, Nature 2001, 409, 387–390;
P. Stano, P. L. Luisi, Cur. Opin. Biotechnol. 2013, 24, 633–638;
F. Capra, P. L. Luisi, The Systems View of Life: A Unifying Vision, Cambridge University Press, Cambridge, 2014;
S. Sarkar, S. Das, S. Dagar, M. P. Joshi, C. Mungi, A. A. Sawant, G. M. Patki, S. Rajamani, J. Membr. Biol. 2020, 253, 589;
I. Gözen, E. S. Köksal, I. Põldsalu, L. Xue, K. Spustova, E. Pedrueza-Villalmanzo, R. Ryskulov, F. Meng, A. Jesorka, Small 2022, 18, 2106624.
P. A. Beales, B. Ciani, A. J. Cleasby, Phys. Chem. Chem. Phys. 2015, 17, 15489–15507;
J. W. Taylor, S. A. Eghtesadi, L. J. Points, T. Liu, L. Cronin, Nat. Commun. 2017, 8, 237;
N. Martin, J.-P. Douliez, ChemSystemsChem 2021, 3, e2100024.
A. Fallah-Araghi, K. Meguellati, J.-C. Baret, A. E. Harrak, T. Mangeat, M. Karplus, S. Ladame, C. M. Marques, A. D. Griffiths, Phys. Rev. Lett. 2014, 112, 028301.
T. M. McCollom, G. Ritter, B. R. T. Simoneit, Origins Life Evol. Biospheres 1999, 29, 153–166;
D. Deamer, J. P. Dworkin, S. A. Sandford, M. P. Bernstein, L. J. Allamandola, Astrobiology 2002, 2, 371–381;
K. Morigaki, P. Walde, Curr. Opin. Colloid Interface 2007, 12, 75–80;
H. J. Cleaves, Evol. Educ. Outreach. 2012, 5, 342–360;
S. Sarkar, S. Dagar, A. Verma, S. Rajamani, Sci. Rep. 2020, 10, 4483.
P. L. Luisi, P. Walde, T. Oberholzer, Curr. Opin. Colloid Interface. 1999, 4, 33–39;
S. S. Mansy, J. W. Szostak, Proc. Natl. Acad. Sci. USA 2008, 105, 13351–13355;
N. Ichihashi, T. Yomo, Life (Basel) 2016, 6, 1–12;
M. Xue, R. A. Black, C. E. Cornell, G. P. Drobny, S. L. Keller, ChemBioChem 2020, 21, 2764–2767.
S. E. Maurer, D. W. Deamer, J. M. Boncella, P. A. Monnard, Astrobiology 2009, 9, 979–987;
C. L. Apel, D. W. Deamer, M. N. Mautner, Biochim. Biophys. Acta Biomembr. 2002, 1559, 1–9.
P. A. Monnard, C. L. Apel, A. Kanavarioti, D. W. Deamer, Astrobiology 2002, 2, 139–152;
T. Namani, D. W. Deamer, Origins Life Evol. Biospheres 2008, 38, 329–341;
K. Adamala, J. W. Szostak, Science. 2013, 342, 1098–1100;
D. Deamer, Life (Basel) 2017, 7, 1–17.
T. Z. Jia, K. Chandru, Y. Hongo, R. Afrin, T. Usui, K. Myojo, H. J. Cleaves, Proc. Natl. Acad. Sci. USA 2019, 116, 15830–15835.
M. Prasad, B. Hazra, A. Sardar, R. Mandal, S. Gayen, P. K. Tarafdar, Soft Matter. 2023, 19, 3884–3894;
M. Prasad, B. Hazra, R. Mandal, S. Das, P. K. Tarafdar, Langmuir. 2023, 39, 9671–9680;
B. Hazra, M. Prasad, R. Roy, P. K. Tarafdar, Org. Biomol. Chem. 2021, 19, 8049–8056;
R. Mandal, A. Ghosh, N. K. Rout, M. Prasad, B. Hazra, S. Sar, S. Das, A. Datta, P. K. Tarafdar, Org. Biomol. Chem. 2023, 21, 4473–4481;
B. Hazra, A. Mondal, M. Prasad, S. Gayen, R. Mandal, A. Sardar, P. K. Tarafdar, Langmuir. 2022, 38, 15422–15432.
S. Murillo-Sánchez, D. Beaufils, J. M. González Mañas, R. Pascal, K. Ruiz-Mirazo, Chem. Sci. 2016, 7, 3406–3413;
E. C. Izgu, A. Björkbom, N. P. Kamat, V. S. Lelyveld, W. Zhang, T. Z. Jia, J. W. Szostak, J. Am. Chem. Soc. 2016, 138, 16669–16676.
Y. Ju, H. Zhang, Y. Jiang, W. Wang, G. Kan, K. Yu, X. Wang, J. Liu, J. Jiang, Nat. Ecol. Evol. 2023, 7, 1892–1902.
Z. Yin, L. Tian, A. J. Patil, M. Li, S. Mann, Angew. Chem. Int. Ed. 2022, 61, e202202302;
P. A. Monnard, P. Walde, Life (Basel, Switzerland) 2015, 5, 1239–1263;
T. Lu, S. Javed, C. Bonfio, E. Spruijt, Small Methods 2023, 7,, 2300294.
S. Koga, D. S. Williams, A. W. Perriman, S. Mann, Nat. Chem. 2011, 3, 720–724;
S. Mann, Acc. Chem. Res. 2012, 45, 2131–2141.
C. M. Dobson, G. B. Ellison, A. F. Tuck, V. Vaida, Proc. Natl. Acad. Sci. USA 2000, 97, 11864–11868.
A. S. Indulkar, Y. Gao, S. A. Raina, G. G. Z. Zhang, L. S. Taylor, Mol. Pharmaceutics. 2016, 13, 2059–2069;
M. Tena-Solsona, C. Wanzke, B. Riess, A. R. Bausch, J. Boekhoven, Nat. Commun. 2018, 9, 2044;
C. D. Keating, R. V. Pappu, J. Phys. Chem. Lett. 2021, 12, 10994–10995.
R. W. Lewis, B. Klemm, M. Macchione, R. Eelkema, Chem. Sci. 2022, 13, 4533–4544.
R. Mandal, K. Mahanty, S. Mandal, S. De Sarkar, P. K. Tarafdar, Chem. Commun. 2021, 57, 11088–11091.
Y. Hattori, M. Kinjo, M. Ishigami, K. Nagano, Origins Life 1984, 14, 145–150;
U. J. Meierhenrich, G. M. Muñoz Caro, J. H. Bredehöft, E. K. Jessberger, W. H. Thiemann, Proc. Natl. Acad. Sci. USA 2004, 101, 9182–9186;
A. P. Johnson, H. J. Cleaves, J. P. Dworkin, D. P. Glavin, A. Lazcano, J. L. Bada, Science 2008, 322, 404.
I. Jiménez-Serra, L. F. Rodríguez-Almeida, J. Martín-Pintado, V. M. Rivilla, M. Melosso, S. Zeng, L. Colzi, Y. Kawashima, E. Hirota, C. Puzzarini, B. Tercero, P. de Vicente, F. Rico-Villas, M. A. Requena-Torres, S. Martín, A&A 2022, 663, 1–15.
I. Lago, L. Black, M. Wilfinger, S. E. Maurer, Membr. (Basel) 2022, 12, 1–7 .
M. P. Joshi, A. A. Sawant, S. Rajamani, Chem. Sci. 2021, 12, 2970–2978;
C. Gibard, S. Bhowmik, M. Karki, E.-K. Kim, R. Krishnamurthy, Nat. Chem. 2018, 10, 212–217;
A. Bhattacharya, L. Tanwar, A. Fracassi, R. J. Brea, M. Salvador-Castell, S. Khanal, S. K. Sinha, N. K. Devaraj, J. Am. Chem. Soc. 2023, 145, 27149-27159 ;
B. Hazra, M. Prasad, S. Das, R. Mandal, A. Sardar, N. Dewangan, P. K. Tarafdar, Langmuir 2023, 39, 17031–17042.
U. J. Meierhenrich, G. M. Muñoz Caro, J. H. Bredehöft, E. K. Jessberger, W. H. P. Thiemann, Proc. Natl. Acad. Sci. USA 2004, 101, 9182–9186.
A. I. Rushdi, B. R. Simoneit, Origins Life Evol. Biospheres 2001, 31, 103–118.
J. N. Israelachvili, in Intermolecular and Surface Forces (Third Edition) (Ed.: J. N. Israelachvili), Academic Press, San Diego, 2011, pp. 535–576.
S. Sarkar, S. Dagar, S. Rajamani, ChemSystemsChem 2021, 3, e2100014.
C. de Gracia Lux, J. Olejniczak, N. Fomina, M. L. Viger, A. Almutairi, J. Polym. Sci. Part A 2013, 51, 3783–3790;
J. S. Mejia, E. R. Gillies, Polym. Chem. 2013, 4, 1969–1982;
R. W. Hay, P. J. Morris, J. Chem. Soc.-Perkin Trans. 2 1972, 1021–1029.
S. K. Kim, S. J. Park, X. H. Li, Y. S. Choi, D. S. Im, J. H. Lee, Environ. Microbiol. 2018, 20, 3992–4008;
O. Geiger, N. González-Silva, I. M. López-Lara, C. Sohlenkamp, Prog. Lipid Res. 2010, 49, 46–60.
A. Lazcano, J. Oró, S. L. Miller, Precambrian Res. 1983, 20, 259–282;
R. W. J. Lim, A. C. Fahrenbach, Pure Appl. Chem. 2020, 92, 1971–1986;
K. Plankensteiner, H. Reiner, B. Schranz, B. M. Rode, Angew. Chem. Int. Ed. 2004, 43, 1886–1888.
R. Ciuraru, L. Fine, M. v. Pinxteren, B. D'Anna, H. Herrmann, C. George, Environ. Sci. Technol. 2015, 49, 13199–13205.
E. Breitmaier, Terpenes: flavors, fragrances, pharmaca, pheromones, John Wiley & Sons, 2006.
J. Gao, C. Wu, Langmuir 2005, 21, 782–785;
D. Cochin, A. Laschewsky, F. Nallet, Macromolecules 1997, 30, 2278–2287.