Page last updated: 2024-12-05

D-proline

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

D-proline, the enantiomer of the common L-proline, is a non-proteinogenic amino acid. It has garnered considerable interest due to its unique properties and potential applications in various fields.

D-proline synthesis typically involves enzymatic or chemical methods, with the latter often employing chiral catalysts to achieve high enantioselectivity. The compound exhibits distinct conformational preferences compared to L-proline, which influences its interactions with other molecules.

Research into D-proline has revealed its potential in fields like pharmaceuticals, materials science, and agriculture. It has been explored as a building block for novel peptides and peptidomimetics, exhibiting therapeutic potential in areas such as cancer treatment and viral inhibition.

D-proline's unique structural features make it a valuable probe for investigating protein structure and function. Its incorporation into peptides can alter their folding, stability, and biological activity, leading to insights into the fundamental principles of protein design and engineering.

In addition, D-proline has been investigated for its potential to enhance the efficiency of biocatalysts. The introduction of D-proline residues into enzymes can modulate their catalytic activity and selectivity, opening avenues for optimizing industrial processes.

D-proline's intriguing properties and potential applications continue to drive research in various areas. Its study provides valuable insights into the structure, function, and manipulation of biomolecules, potentially leading to the development of new drugs, materials, and technologies.'

Cross-References

ID SourceID
PubMed CID8988
CHEMBL ID80257
CHEBI ID16313
SCHEMBL ID65555

Synonyms (60)

Synonym
CHEMBL80257
CHEBI:16313 ,
(2r)-pyrrolidine-2-carboxylic acid
(r)-2-carboxypyrrolidine
d-prolin
(r)-pyrrolidine-2-carboxylic acid
d-pro
C00763
344-25-2
D-PROLINE ,
d-proline, reagentplus(r), >=99%
DB02853
NCGC00163339-02
NCI97923
NCGC00163339-01
NCISTRUC1_001918
NCISTRUC2_000132
P-7200
D2735F99-0D23-48C4-B266-5C7A7DA319A4
d-(+)-proline
h-d-pro-oh
P0994
h-pros-oh
d-d-pro-oh
AKOS015923206
pyrrolidine-2-carboxylic acid;d-proline
CCG-37784
l01q4lgz5l ,
unii-l01q4lgz5l
einecs 206-452-7
bdbm50357224
AM20090537
S6016
gtpl4676
SCHEMBL65555
mfcd00064317
pyrrolidine-2-(r)-carboxylic acid
(r)-proline
r-proline
ONIBWKKTOPOVIA-SCSAIBSYSA-N
(d)-proline
h-dpro-oh
J-300218
TS-01590
CS-W020557
d-2-pyrrolidinecarboxylic acid
AC-24083
F1905-6974
(r)-pyrrolidine-2-carboxylate
r)-2-carboxypyrrolidine
d-proline, vetec(tm) reagent grade, 98%
HY-75087
(+)-(r)-proline
proline, d-
1331908-17-8
Q20035962
DTXSID70883367
STARBLD0002768
EN300-60161
Z933632584
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
D-alpha-amino acid zwitterionZwitterionic form of a D-alpha-amino acid having an anionic carboxy group and a protonated amino group.
D-alpha-amino acid
prolineAn alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (13)

PathwayProteinsCompounds
Arginine and Proline Metabolism2047
Prolidase Deficiency (PD)2047
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)2047
Hyperprolinemia Type II2047
Hyperprolinemia Type I2047
Prolinemia Type II2047
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)2047
Ornithine Aminotransferase Deficiency (OAT Deficiency)2047
Creatine Deficiency, Guanidinoacetate Methyltransferase Deficiency2047
Hyperornithinemia with Gyrate Atrophy (HOGA)2047
Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome]2047
L-Arginine:Glycine Amidinotransferase Deficiency2047
Biochemical pathways: part I0466

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
phosphopantetheinyl transferaseBacillus subtilisPotency44.66840.141337.9142100.0000AID1490
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (10)

Processvia Protein(s)Taxonomy
monoatomic ion transportProton-coupled amino acid transporter 1Homo sapiens (human)
amino acid transportProton-coupled amino acid transporter 1Homo sapiens (human)
taurine transmembrane transportProton-coupled amino acid transporter 1Homo sapiens (human)
proline transportProton-coupled amino acid transporter 1Homo sapiens (human)
alanine transportProton-coupled amino acid transporter 1Homo sapiens (human)
amino acid import across plasma membraneProton-coupled amino acid transporter 1Homo sapiens (human)
glycine transportProton-coupled amino acid transporter 1Homo sapiens (human)
proline transmembrane transportProton-coupled amino acid transporter 1Homo sapiens (human)
proton transmembrane transportProton-coupled amino acid transporter 1Homo sapiens (human)
L-alanine transportProton-coupled amino acid transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
amino acid:proton symporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
proline:proton symporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
taurine transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
protein bindingProton-coupled amino acid transporter 1Homo sapiens (human)
amino acid transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
alanine transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
L-alanine transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
L-proline transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
glycine transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
lysosomal membraneProton-coupled amino acid transporter 1Homo sapiens (human)
endoplasmic reticulumProton-coupled amino acid transporter 1Homo sapiens (human)
plasma membraneProton-coupled amino acid transporter 1Homo sapiens (human)
apical plasma membraneProton-coupled amino acid transporter 1Homo sapiens (human)
vacuolar membraneProton-coupled amino acid transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID630741Inhibition of human PAT1-mediated L-[3H]proline uptake in human Caco2 cells after 10 mins by liquid scintillation counting2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Three-dimensional quantitative structure-activity relationship analyses of substrates of the human proton-coupled amino acid transporter 1 (hPAT1).
AID143623Inhibitory concentration required to inhibit [3H]strychnine binding to N-methyl-D-aspartate glutamate receptor 11992Journal of medicinal chemistry, Jan-24, Volume: 35, Issue:2
Beta-proline analogues as agonists at the strychnine-sensitive glycine receptor.
AID1751497Antibiofilm activity against Staphylococcus aureus assessed as inhibition of biofilm formation at 500 uM2021Bioorganic & medicinal chemistry letters, 09-15, Volume: 48Discovery of non-proteinogenic amino acids inhibiting biofilm formation by S. aureus and methicillin-resistant S. aureus.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (20.00)18.2507
2000's0 (0.00)29.6817
2010's1 (20.00)24.3611
2020's3 (60.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 39.74

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index39.74 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index51.54 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (39.74)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]