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Cited by 76Amino Acid Enzymes and MetabolismBacterial Genetics and BiotechnologyMicrobial Natural Products and Biosynthesis

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Occurrence of peptidyl d-amino acids in soluble fractions of several eubacteria, archaea and eukaryotes

Nagata, Yoko, Fujiwara, Taketomo, Kawaguchi-Nagata, Kumiko, Yoshihiro Fukumori, Yamanaka, Tateo·1998·Biochimica et Biophysica Acta (BBA) - General Subjects
DOI 10.1016/s0304-4165(97)00084-6
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Abstract

The occurrence of peptidyl D-amino acids in the aqueous soluble fractions was investigated in various eubacteria, some archaea and some eukaryotes. The contents of the D-enantiomers of serine, alanine, proline, glutamate (glutamine), aspartate (asparagine) and phenylalanine were determined with cell- and tissue-extracts, by means of acid hydrolysis and high-performance liquid chromatography. The rate of D-enantiomer (%, the ratio in molar concentration of a D-amino acid to the total of the D-amino acid and the corresponding L-amino acid) of alanine and glutamate were high in some Gram-positive eubacteria: 11.7% in Staphylococcus epidermidis and 10.3% in Streptococcus pyogenes for alanine, and 22.3% for glutamate in Bacillus YN-1. The D-glutamate content was also high (8.0%) in the Gram-negative eubacterium, Thiobacillus ferrooxidans. D-Aspartate was common, as was D-glutamate: the highest D-aspartate content was detected in an archaeum, Pyrobaculum islandicum (4.0%). However, the content of D-aspartate was low, 0.2-1.8% in most other bacteria. The presence of D-serine was shown in some organisms, but that of D-proline was scarce. The D-enantiomer of phenylalanine was not detected in any of the organisms examined. These results indicate that of the bacteria examined herein most Gram-negative and some Gram-positive eubacteria, as well as archaea contain only low levels of D-amino acids in the soluble peptidyl fraction, and the levels were comparable to those in eukaryotes examined. To our knowledge, the general presence of peptidyl D-amino acids in these organisms, especially archaea and eukaryotic cells including those from rat liver tissues, has been shown here for the first time.

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  • (R)-amino acids have been detected in the cell wall peptidoglycan layer of bacteria and in various peptides of bacteria, archaea, and eukaryotes.

    “On the other side, (R)-amino acids have been detected in the cell wall peptidoglycan layer of bacteria 585 and in various peptides of bacteria, archaea, and eukaryotes.”

    From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [16]

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Metadata

Authors
Nagata, Y., Fujiwara, T., Kawaguchi-Nagata, K., Fukumori, Y., & Yamanaka, T.
Affiliations
  • Tokyo Institute of Technology (JP)
  • Nihon University (JP)
Corresponding author
Nagata, Yoko
ORCID
Fujiwara, Taketomo
Venue
Biochimica et Biophysica Acta (BBA) - General Subjects
Publisher
Elsevier BV
Published
1998-01
Volume
1379
Issue
1
Pages
76-82
ISSN
0304-4165 (ISSN-L)
DOI
10.1016/s0304-4165(97)00084-6
OpenAlex
W2027880438
Cited by
76
References
0
Citations by year
2025: 2 · 2024: 1 · 2023: 1 · 2022: 1 · 2021: 2 · 2019: 3 · 2018: 3 · 2017: 3 · 2016: 3 · 2015: 5 · 2014: 2 · 2013: 3 · 2012: 2
FWCI
2.38
Type
journal article
Language
en
Open access
closed
Licence
Locations
  • Biochimica et Biophysica Acta (BBA) - General Subjects (publishedVersion)
  • PubMed (publishedVersion)
Funders
Ministry of Education, Culture, Sports, Science and Technology
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Amino Acid Enzymes and Metabolism
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Genetics › Bacterial Genetics and Biotechnology
  • Life Sciences › Immunology and Microbiology › Applied Microbiology and Biotechnology › Microbial Natural Products and Biosynthesis
Keywords
D-amino acids, D-alanine, D-glutamic acid, D-aspartate, D-serine, D-proline, D-phenylalanine, eubacteria, archaea, eukaryotes, rat liver, Staphylococcus epidermidis, Streptococcus pyogenes, Bacillus, Acidithiobacillus ferrooxidans, Pyrobaculum islandicum, Gram-positive bacteria, Gram-negative bacteria
MeSH terms
Amino Acids, Archaea, Bacteria, Chromatography, High Pressure Liquid, Eukaryotic Cells, Gram-Negative Bacteria, Gram-Positive Bacteria, Peptides, Stereoisomerism

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