Vaccine Lab / Alfa Chemistry
Proline

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Proline

Catalog Number ACM147853-1
CAS 147-85-3
Structure
Synonyms L-Proline
IUPAC Name (2S)-Pyrrolidine-2-carboxylic acid
Molecular Weight 115.13
Molecular Formula C5H9NO2
Canonical SMILES C1CC(NC1)C(=O)O
InChI InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1
InChI Key ONIBWKKTOPOVIA-BYPYZUCNSA-N
Boiling Point 215.41 °C
Melting Point 228 °C
Purity 95%+
Density 1.35 g/mL at 25 °C(lit.)
Solubility Soluble in water; insoluble in ether
Complexity 103
Covalently-Bonded Unit Count 1
Defined Atom Stereocenter Count 1
Exact Mass 115.06332853
Heavy Atom Count 8
Hydrogen Bond Acceptor Count 3
Hydrogen Bond Donor Count 2
Isomeric SMILES C1C[C@H](NC1)C(=O)O
Monoisotopic Mass 115.06332853
Physical State Powder
Rotatable Bond Count 1
Storage Conditions 2-8 °C
Topological Polar Surface Area 49.3 Ų
Knowledge & Learning Case Study Q&A

Proline: An Essential Stabilizer in Vaccine Development

Proline is used as a stabilizer in vaccines because of its unique structure, which helps prevent protein denaturation and aggregation. Furthermore, the contribution of proline to enhanced immunogenicity is another important aspect of its application in vaccines. Get more information on:

  • About Proline
  • Application of Proline in Vaccines
  • Proline as a Stabilizer
  • Proline in Immunogenicity Enhancement
  • Proline Stabilization Method for Viral Vaccine Development

What is the chemical symbol for proline?

The chemical symbol for proline is Pro or P.

How is proline classified in terms of amino acids?

Proline is classed as a proteinogenic amino acid, used in the biosynthesis of proteins.

Does proline contain an amino group?

No, proline does not contain the amino group -NH2, but rather a secondary amine.

What forms do the nitrogen and carboxyl group of proline take under biological conditions?

The nitrogen is in the protonated form (NH2+), while the carboxyl group is in the deprotonated (-COO-) form.

How is proline's "side chain" connected to the α carbon?

The "side chain" from the α carbon connects to the nitrogen, forming a pyrrolidine loop.

Is proline essential or non-essential in humans?

Proline is non-essential in humans, meaning the body can synthesize it from the non-essential amino acid L-glutamate.

What are the codons that encode proline?

Proline is encoded by all the codons starting with CC (CCU, CCC, CCA, and CCG).

How is proline biosynthetically derived from L-glutamate?

Glutamate-5-semialdehyde is first formed by glutamate 5-kinase and glutamate-5-semialdehyde dehydrogenase. It can then either spontaneously cyclize or be turned into ornithine before cyclization to form proline.

What biological activities does L-Proline exhibit?

L-Proline has been found to act as a weak agonist of the glycine receptor and of both NMDA and non-NMDA (AMPA/kainate) ionotropic glutamate receptors. It has also been proposed as a potential endogenous excitotoxin.

What are some uses of proline?

Proline and its derivatives are used as asymmetric catalysts in proline organocatalysis reactions. It is also used in brewing to produce haze and as an osmoprotectant in pharmaceutical and biotechnological applications. Additionally, proline can be used to supplement the growth medium in plant tissue culture to increase growth and tolerance to stresses.

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