PMID- 36697941
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20230202
IS  - 2399-3669 (Electronic)
IS  - 2399-3669 (Linking)
VI  - 5
IP  - 1
DP  - 2022 Nov 9
TI  - Elucidating N-acyl amino acids as a model protoamphiphilic system.
PG  - 147
LID - 10.1038/s42004-022-00762-9 [doi]
LID - 147
AB  - Protoamphiphiles are prebiotically-plausible moieties that would have constituted 
      protocell membranes on early Earth. Although prebiotic soup would have contained 
      a diverse set of amphiphiles capable of generating protocell membranes, earlier 
      studies were mainly limited to fatty acid-based systems. Herein, we characterize 
      N-acyl amino acids (NAAs) as a model protoamphiphilic system. To the best of our 
      knowledge, we report a new abiotic route in this study for their synthesis under 
      wet-dry cycles from amino acids and monoglycerides via an ester-amide exchange 
      process. We also demonstrate how N-oleoyl glycine (NOG, a representative NAA) 
      results in vesicle formation over a broad pH range when blended with a 
      monoglyceride or a fatty acid. Notably, NOG also acts as a substrate for peptide 
      synthesis under wet-dry cycles, generating different lipopeptides. Overall, our 
      study establishes NAAs as a promising protoamphiphilic system, and highlights 
      their significance in generating robust and functional protocell membranes on 
      primitive Earth.
CI  - (c) 2022. The Author(s).
FAU - Joshi, Manesh Prakash
AU  - Joshi MP
AUID- ORCID: 0000-0003-2718-4033
AD  - Department of Biology, Indian Institute of Science Education and Research Pune, 
      Pune, 411008, India. manesh.joshi@students.iiserpune.ac.in.
FAU - Uday, Ashwin
AU  - Uday A
AD  - Department of Biology, Indian Institute of Science Education and Research Pune, 
      Pune, 411008, India.
FAU - Rajamani, Sudha
AU  - Rajamani S
AUID- ORCID: 0000-0002-6030-495X
AD  - Department of Biology, Indian Institute of Science Education and Research Pune, 
      Pune, 411008, India. srajamani@iiserpune.ac.in.
LA  - eng
GR  - CRG/2021/001851/DST | Science and Engineering Research Board (SERB)/
PT  - Journal Article
DEP - 20221109
PL  - England
TA  - Commun Chem
JT  - Communications chemistry
JID - 101725670
PMC - PMC9814278
COIS- The authors declare no competing interests.
EDAT- 2023/01/26 06:00
MHDA- 2023/01/26 06:01
PMCR- 2022/11/09
CRDT- 2023/01/25 23:48
PHST- 2022/07/13 00:00 [received]
PHST- 2022/10/19 00:00 [accepted]
PHST- 2023/01/25 23:48 [entrez]
PHST- 2023/01/26 06:00 [pubmed]
PHST- 2023/01/26 06:01 [medline]
PHST- 2022/11/09 00:00 [pmc-release]
AID - 10.1038/s42004-022-00762-9 [pii]
AID - 762 [pii]
AID - 10.1038/s42004-022-00762-9 [doi]
PST - epublish
SO  - Commun Chem. 2022 Nov 9;5(1):147. doi: 10.1038/s42004-022-00762-9.