Abstract
Naturally occurring secondary amino acids, with proline as the main representative, contain an alpha-imino group in a cycle that is typically four-, five-, and six-membered. The unique ring structure exhibits exceptional properties—conformational rigidity, chemical stability, and specific roles in protein structure and folding. Many proline analogues have been used as valuable compounds for the study of metabolism of both prokaryotic and eukaryotic cells and for the synthesis of compounds with desired biological, pharmaceutical, or industrial properties. The d-forms of secondary amino acids play different roles in living organisms than the l-forms. They have different metabolic pathways, biological, physiological, and pharmacological effects, they can be indicators of changes and also serve as biomarkers of diseases. In the scientific literature, the number of articles examining d-amino acids in biological samples is increasing. The review summarises information on the occurrence and importance of d- and l-secondary amino acids—azetidic acid, proline, hydroxyprolines, pipecolic, nipecotic, hydroxypipecolic acids and related peptides containing these d-AAs, as well as the main analytical methods (mostly chromatographic) used for their enantiomeric determination in different matrices (biological samples, plants, food, water, and soil).
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Abbreviations
- 2D-PC:
-
Two-dimensional paper chromatography
- 2D-HPLC:
-
Two-dimensional high-performance liquid chromatography
- 3c-L-Hyp:
-
cis-3-Hydroxy-l-proline, ((2S,3R)-3-Hydroxypyrrolidine-2-carboxylic acid)
- 3t-L-Hyp:
-
trans-3-Hydroxy-l-proline, ((2S,3S)-3-Hydroxypyrrolidine-2-carboxylic acid)
- 3c-D-Hyp:
-
cis-3-Hydroxy-d- proline ((2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid)
- 3t-D-Hyp:
-
trans-3-Hydroxy-d- proline ((2R,3R)-3-hydroxypyrrolidine-2-carboxylic acid)
- 4c-L-Hyp:
-
cis-4-Hydroxy-l- proline ((2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acid)
- 4t-L-Hyp:
-
trans-4-Hydroxy-l- proline ((2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid)
- 4c-D-Hyp:
-
cis-4-Hydroxy-d- proline ((2R,4R)-4-Hydroxypyrrolidine-2-carboxylic acid)
- 4t-D-Hyp:
-
trans-4-Hydroxy-d- proline ((2R,4S)-4-Hydroxypyrrolidine-2-carboxylic acid)
- 3c-L-HyPip:
-
cis-3-Hydroxy-l-pipecolic acid ((2S, 3R)-3-Hydroxypiperidine-2-carboxylic acid)
- 3t-L-HyPip:
-
trans-3-Hydroxy-l- pipecolic acid ((2S,3S)-3-Hydroxypiperidine-2-carboxylic acid)
- 3c-D-HyPip:
-
cis-3-Hydroxy-d- pipecolic acid ((2R, 3S)-3-Hydroxypiperidine-2-carboxylic acid)
- 3t-D-HyPip:
-
trans-3-Hydroxy-d- pipecolic acid ((2R, 3R)-3-Hydroxypiperidine-2-carboxylic
- 4c-L-HyPip:
-
cis-4-Hydroxy-l- pipecolic acid ((2S,4R)-4-Hydroxypiperidine-2-carboxylic acid)
- 4t-L-HyPip:
-
trans-4-Hydroxy-l- pipecolic acid ((2S,4S)-4-Hydroxypiperidine-2-carboxylic acid)
- 4c-D-HyPip:
-
cis-4-Hydroxy-d- pipecolic acid ((2R,4S)-4-Hydroxypiperidine-2-carboxylic acid)
- 4t-D-HyPip:
-
trans-4-Hydroxy-d- pipecolic acid ((2R,4R)-4-Hydroxypiperidine-2-carboxylic acid)
- 5c-L-HyPip:
-
cis-5-Hydroxy-l- pipecolic acid ((2S,5S)-5-Hydroxypiperidine-2-carboxylic acid)
- 5t-L-HyPip:
-
trans-5-Hydroxy-l- pipecolic acid ((2S,5R)-5-Hydroxypiperidine-2-carboxylic acid)
- AA(s):
-
Amino acid(s)
- AcCl:
-
Acetyl chloride
- AQC:
-
6-Aminoquinolyl-N-hydroxysuccinimidyl carbamate
- AMBI:
-
1-Phenylethylisothiocyanate, alpha-Methylbenzyl isothiocyanate
- BSTFA:
-
N,O-Bis(trimethylsilyl)trifluoroacetamide
- CLEC:
-
Chiral ligand-exchange chromatography
- CSP:
-
Chiral stationary phase
- DAD:
-
Diode array detector
- DCl:
-
: Deuterium chloride
- ddY/DAO:
-
Mutant strain lacking d-Amino acid oxidase activity
- diHyPip:
-
Dihydroxy pipecolic acid
- DMT-(S)-Pro-OSu:
-
(S)-2,5-Dioxopyrrolidin-1-yl-1-(4,6-dimethoxy-1,3,5-triazin-2-yl) pyrrolidine-2-carboxylate
- D-Aze:
-
d-Azetidic acid, d-Azetidine-2-carboxylic acid, ((2R)-Azetidine-2-carboxylic acid)
- L-Aze:
-
l- Azetidic acid, l-Azetidine-2-carboxylic acid, ((2S)-Azetidine-2-carboxylic acid)
- D-Nip:
-
d-Nipecotic acid, ((3R)-Piperidine-3-carboxylic acid)
- L-Nip:
-
l- Nipecotic acid, ((3S)-Piperidine-3-carboxylic acid)
- D-Pip:
-
d-Pipecolic acid, ((2R)-Piperidine-2-carboxylic acid, d-Homoproline)
- L-Pip:
-
l- Pipecolic acid, ((2S)-Piperidine-2-carboxylic acid, l-Homoproline)
- D-Pro:
-
d- Proline, ((2R)-Pyrrolidine-2-carboxylic acid)
- L-Pro:
-
l- Proline, ((2S)-Pyrrolidine-2-carboxylic acid)
- EC:
-
Enzyme Commission number
- EtOD:
-
Ethanol-OD
- FDAA:
-
Marfey’s reagent, 1-Fluoro-2,4-dinitrophenyl-5-l-alanine amide
- FDVA:
-
Nα -(2,4-dinitro-5-fluorophenyl)-d or l-valine amide
- FDLA:
-
Nα -(2,4-dinitro-5-fluorophenyl)-d or l-leucine amide
- FITC:
-
Fluorescein isothiocyanate
- FoPip4H:
-
l-Pip trans-4-hydroxylase of Fusarium oxysporum
- FLEC:
-
1-(9-Fluorenyl)ethyl chloroformate
- FMOC-Cl:
-
9-Fluorenylmethoxycarbonyl chloride, 9-Fluorenylmethyl chloroformate
- GABA:
-
γ-Amino butyric acid
- GC/FID:
-
Gas chromatography with flame ionization detector
- GC/MS:
-
Gas chromatography with mass spectrometric detector
- GITC:
-
2,3,4,6-Tetra-O-acetyl-β -d-glucopyranosyl isothiocyanate
- HFBCF:
-
2,2,3,3,4,4,4-Heptafluorobutyl chloroformate
- Hyp(s):
-
Hydroxyproline (s)
- HyPip(s):
-
Hydroxypipecolic acid (s)
- HPLC:
-
High-performance liquid chromatography
- HPLC/DAD:
-
HPLC with diode array detector
- HPLC/Fl:
-
HPLC with fluorescence detector
- HPLC/UV:
-
HPLC with UV detector
- IBDC:
-
N-Isobutyryl-d-cysteine
- IBLC:
-
N-Isobutyryl-l-cysteine
- IRMPD:
-
Infrared multiple photon dissociation spectroscopy
- HPLC/MS:
-
Liquid chromatography–mass spectrometry
- HPLC/MSMS:
-
Liquid chromatography–tandem mass spectrometry
- MSTFA:
-
N-Methyl-N-(trimethylsilyl)trifluoroacetamide
- NBD-F:
-
4-Fluoro-7-nitro-2,1,3-benzoxadiazole
- NBD-PyNCS:
-
4-(3-Isothiocyanatopyrrolidin-1-yl)-7-nitrobenzofurazan
- N-HyPip:
-
N-Hydroxypipecolic acid, 1-Hydroxypiperidine-2-carboxylic acid
- NIFE:
-
N-(4-Nitrophenoxycarbonyl)-l-phenylalanine-2-methoxyethyl ester
- NMR:
-
Nuclear magnetic resonance
- OPA:
-
o-Phthaldialdehyde
- PFPA:
-
Pentafluoropropionic anhydride
- P5C:
-
Pyrroline-5-carboxylate
- PCA:
-
Pyroglutamic acid
- R(-)-DBD-PyNCS:
-
R(-)-4-(3-Isothiocyanatopyrrolidin-1-yl)-7-(N,N-dimethylaminosulfonyl)-2,1,3-bezoxadiazole
- S( +)-DBD-PyNCS:
-
S( +)-4-(3-Isothiocyanatopyrrolidin-1-yl)-7-(N,N-dimethylaminosulfonyl)-2,1,3-bezoxadiazole
- SFC/MS:
-
Supercritical fluid chromatography–mass spectrometry
- SPE:
-
Solid phase extraction
- TFA:
-
Trifluoroacetic anhydride
- TLC:
-
Thin-layer chromatography
- UPLC:
-
Ultra-performance liquid chromatography
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Zahradníčková, H., Opekar, S., Řimnáčová, L. et al. Chiral secondary amino acids, their importance, and methods of analysis. Amino Acids 54, 687–719 (2022). https://doi.org/10.1007/s00726-022-03136-6
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DOI: https://doi.org/10.1007/s00726-022-03136-6