DL-proline

Also known as Pro, P, pyrrolidine-2-carboxylic acid, Proline, Hpro, proline

thumb|Proline ball and stick model spinning Proline (symbol Pro or P) is an organic acid classed as a proteinogenic amino acid (used in the biosynthesis of proteins), although it does not contain the amino group but is rather a secondary amine. The secondary amine nitrogen is in the protonated form (NH2+) under biological conditions, while the carboxyl group is in the deprotonated −COO− form. The "side chain" from the α carbon connects to the nitrogen forming a pyrrolidine loop, classifying it as a aliphatic amino acid. It is non-essential in humans, meaning the body can synthesize it from the

OverviewAI-generated

DL-proline is a chemical compound with the molecular formula C₅H₉NO₂. Its IUPAC name is pyrrolidin-1-ium-2-carboxylate. The substance has a mass of 115.063 and a melting point of 221. It possesses a pKa value of 1.99 and a canonical SMILES notation of C1CC(NC1)C(=O)O.

Chemical properties include an xlogp of -1.9 and a topological polar surface area of 56.7. The molecule features one hydrogen bond donor and two hydrogen bond acceptors, with a net charge of 0. Its PubChem weight is listed as 115.13. DL-proline is referenced by 1,655 other encyclopedia articles.

Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula: C5H9NO2
Molecular weight: 115.13 g/mol
IUPAC name: pyrrolidin-1-ium-2-carboxylate
SMILES: C1CC([NH2+]C1)C(=O)[O-]
InChIKey: ONIBWKKTOPOVIA-UHFFFAOYSA-N
XLogP: -1.9
Polar surface area: 56.7 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

65 papers

DL-Proline.Acta crystallographica. Section C, Crystal structure communications · 2005Myung S, Pink M, Baik MH et al.DOI: 10.1107/S0108270105021001
Dichlorobis(DL-proline-kappaO)zinc(II).Acta crystallographica. Section C, Crystal structure communications · 2003Lutz M, Bakker RDOI: 10.1107/s0108270102021832
Microbial Proline Racemase-Proline Dehydrogenase Cascade for Efficient Production of D-proline and N-boc-5-hydroxy-L-proline from L-proline.Applied biochemistry and biotechnology · 2022Zhang F, Xia S, Lin H et al.DOI: 10.1007/s12010-022-03980-y
Study on vapor-liquid equilibrium and microscopic properties of DL-proline, L-glutamic acid, and L-serine aqueous solutions.Frontiers in chemistry · 2022Liu W, Zhou Y, Xu XDOI: 10.3389/fchem.2022.1005291
Unexpected proline coordination in the copper chain polymer [Cu(μ-Cl)₂(μ-DL-proline-κ²O:O')]¹∞.Acta crystallographica. Section C, Structural chemistry · 2015Lamberts K, Şerb MD, Englert UDOI: 10.1107/S205322961500426X
Retrograde amnesia in chicks and mice induced by 3,4-dehydro-DL-proline, a proline analog.Pharmacology, biochemistry, and behavior · 1979Davis JL, Cherkin ADOI: 10.1016/0091-3057(79)90314-9
The use of hydroxy-DL-proline-2-(14)C in the investigation of hydroxyproline metabolism in normal subjects and in patients with renal insufficiency.Clinical nephrology · 1976Hart W, van den Hamer CJ, van der Sluys Veer J
Potential inhibitors of collagen biosynthesis, 4,4-Difluoro-L-proline and 4,4-dimethyl-DL-proline and their activation by prolyl-tRNA ligase.Journal of medicinal chemistry · 1977Shirota FN, Nagasawa HT, Elberling JADOI: 10.1021/jm00219a013

via PubMed

~9 min read

Encyclopedic overview

12 sections

Contents

History and etymology
Biosynthesis
Biological activity
Properties in protein structure
''Cis''–''trans'' isomerization
Uses
Specialties
Synthesis
See also
References
Further reading
External links

Proline is the only proteinogenic amino acid which is a secondary amine, as the nitrogen atom is attached both to the α-carbon and to a chain of three carbons that together form a five-membered ring.

Excerpted from Wikipedia’s “DL-proline” article, available under the CC BY-SA 4.0 licence.