Isolation of L-3-phenyllactyl-Leu-Arg-Asn-NH sub 2 (Antho-RNamide), a sea anemone neuropeptide containing an unusual amino-terminal blocking group

Journal Article · Sun Jul 01 00:00:00 EDT 1990 · Proceedings of the National Academy of Sciences of the United States of America; (USA)

DOI:https://doi.org/10.1073/pnas.87.14.5410· OSTI ID:6151413

Grimmelikhuijzen, C J.P.; Jacob, E; Graff, D; Reinscheid, R K; Nothacker, H P ^[1]; Rinehart, K L; Staley, A L ^[2]

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1. Univ. of Hamburg (West Germany)
2. Univ. of Illinois, Urbana (USA)

Using a radioimmunoassay for the carboxyl-terminal sequence Arg-Asn-NH{sub 2}, the authors have purified a peptide from acetic acid extracts of the sea anemone Anthopleura elegantissima. By classical amino acid analyses, mass spectrometry, and {sup 1}H NMR spectroscopy, the structure of this peptide was determined as 3-phenyllactyl-Leu-Arg-Asn-NH{sub 2}. By using reversed-phase HPLC and a chiral mobile phase, it was shown that the 3-phenyllactyl group had the L configuration. Immunocytochemical staining with antiserum against Arg-Asn-NH{sub 2} showed that L-3-phenyllactyl-Leu-Arg-Asn-NH{sub 2} (Antho-RNamide) was localized in neutrons of sea anemones. The L-3-phenyllactyl group has not been found earlier in neuropeptides of vertebrates or higher invertebrates. They propose that this residue renders Antho-RNamide resistant to nonspecific aminopeptidases, thereby increasing the stability of the peptide after neuronal release.

• OSTI ID: 6151413
• Journal Information: Proceedings of the National Academy of Sciences of the United States of America; (USA), Vol. 87:14; ISSN 0027-8424
• Country of Publication: United States
• Language: English

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59 BASIC BIOLOGICAL SCIENCES
NEUROREGULATORS
NUCLEAR MAGNETIC RESONANCE
PEPTIDES
RADIOIMMUNOASSAY
AMINOPEPTIDASES
CYTOCHEMISTRY
INVERTEBRATES
ION EXCHANGE CHROMATOGRAPHY
NERVE CELLS
PROTONS
ANIMAL CELLS
ANIMALS
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BARYONS
BIOASSAY
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CHEMISTRY
CHROMATOGRAPHY
DIAGNOSTIC TECHNIQUES
DRUGS
ELEMENTARY PARTICLES
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FERMIONS
HADRONS
HYDROLASES
IMMUNOASSAY
IMMUNOLOGY
ISOTOPE APPLICATIONS
MAGNETIC RESONANCE
NUCLEONS
ORGANIC COMPOUNDS
PEPTIDE HYDROLASES
PROTEINS
RADIOASSAY
RADIOIMMUNODETECTION
RADIOIMMUNOLOGY
RESONANCE
SEPARATION PROCESSES
SOMATIC CELLS
TRACER TECHNIQUES
550201* - Biochemistry- Tracer Techniques