L-Prolin

Bezeichnung:L-Prolin

CAS-Nr147-85-3

Englisch Name:L-Proline

CBNumberCB6118196

SummenformelC5H9NO2

Molgewicht115.13

MOL-Datei147-85-3.mol

Synonyma

L-Prolin

L-Prolin physikalisch-chemischer Eigenschaften

Schmelzpunkt	228 °C (dec.) (lit.)
Siedepunkt	215.41°C (rough estimate)
alpha	-85.5 º (c=4, H2O)
Dichte	1.35
Dampfdruck	0Pa at 25℃
FEMA	3319 \| L-PROLINE
Brechungsindex	-85 ° (C=4, H2O)
storage temp.	2-8°C
Löslichkeit	H₂O: 50 mg/mL
Aggregatzustand	powder
pka	1.95, 10.64(at 25℃)
Farbe	White
Geruch (Odor)	at 100.00 %. odorless
PH	6.0-7.0 (25℃, 1M in H2O)
Optische Aktivität	[α]20/D 85.0±1.0°, c = 5% in H2O
Geruchsart	odorless
Wasserlöslichkeit	soluble
Sensitive	Hygroscopic
maximale Wellenlänge (λmax)	λ: 260 nm Amax: 0.05 λ: 280 nm Amax: 0.05
JECFA Number	1425
Merck	14,7780
BRN	80810
Stabilität	Stable. Incompatible with strong oxidizing agents.
InChIKey	ONIBWKKTOPOVIA-UHFFFAOYSA-N
LogP	-2.54 at 20℃
CAS Datenbank	147-85-3(CAS DataBase Reference)
NIST chemische Informationen	Proline(147-85-3)
EPA chemische Informationen	L-Proline (147-85-3)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	36/37/38-22
S-Sätze:	24/25-36/37/39-26
WGK Germany	3
RTECS-Nr.	TW3584000
F	3-10
TSCA	Yes
HS Code	29339990
Giftige Stoffe Daten	147-85-3(Hazardous Substances Data)
Toxizität	LD50 orally in Rabbit: > 5110 mg/kg

Gefahreninformationscode (GHS)

L-Proline Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Chemische Eigenschaften
L-Proline, an amino acid, is colorless to white crystal or crystalline powder that has a slight, characteristic odor with a slightly sweet taste. It is soluble in water, insoluble in ethanol, diethyl ether and n-butanol, yellow in case of hydrated ninhydrin test solution, glacial acetic acid Red after acidification; pH=6.3, decomposition point is 220-222°C; specific optical rotation [α]20D-85° (0.5-2.0mg/ml, H2O), [α]20D-60.4° (0.5-2.0mg /ml, 5mol/LHCl). It is synthesized from L-glutamine and L-glutamate via L-ornithine in intestine, and from L-ornithine in liver. It is widely used as an ingredient in infusion and infant formula.
Occurrence
Reported found as a component in many proteins; also widely occurring as the free acid in natural products. A major constituent of collagen, the main fibrous protein found in bone, cartilage and other connective tissue.
Verwenden
L-Proline is an amino acid and precursor (with vitamin C) for collagen, the building block of the structure of tendons, ligaments, arteries, veins and muscles. It is important in wound healing.
Verwenden
L-Proline is used as asymmetric catalysts in organic synthesis and asymmetric aldol cyclization. It is involved in the Michael addition of dimethyl malonate to alfa-beta-unsaturated aldehydes. It is a precursor of hydroxyproline in collagen. It is an active component of collagen and involved in the proper functioning of joints and tendons. It finds uses in pharmaceutical, biotechnological applications due to its osmoprotectant property. Further, it is used with ninhydrin in the chromatography.
synthetische
Synthesis of L-proline: Using glutamic acid as a raw material, it is esterified with absolute ethanol under the catalysis of sulfuric acid, and triethanolamine is added to free the aminosulfate to obtain glutamic acid-δ-ethyl ester. The glutamic acid-δ-ethyl ester is then reduced with a metal reducing agent potassium borohydride to obtain crude proline, which is finally separated and purified to obtain crude L-proline.
Definition
ChEBI: L-proline is pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group alpha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles. It has a role as a micronutrient, a nutraceutical, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a mouse metabolite and a member of compatible osmolytes. It is a glutamine family amino acid, a proteinogenic amino acid, a proline and a L-alpha-amino acid. It is a conjugate base of a L-prolinium. It is a conjugate acid of a L-prolinate. It is an enantiomer of a D-proline. It is a tautomer of a L-proline zwitterion.
Biotechnologische Produktion
Direct fermentation using analogue-resistant mutants of coryneform bacteria or Serratia marcescens is an economic production method. An isoleucine auxotrophic mutant of Brevibacterium flavum having resistance to sulfaguanidine and D,L-3,4-dehydroproline (DP) is able to accumulate 40 g/L L-proline. Brevibacterium flavum AP113 is claimed to produce 97.5 g/L L-proline; this mutant is characterized by isoleucine auxotrophy, resistance to DP, and osmotic pressure and incapable to degrade Lproline. A proline oxidase-less strain of Serratia marcescens, having resistance to DP, thiazoline-4-carboxylate and azetidine-2-carboxylate, overproduces 58.5 g/L L-proline into the culture medium. By amplification of the genes proA and proB in this type of regulatory mutant, a construct was obtained which yields 75 g/L L-proline.
benefits
L-proline is considered a non-essential amino acid as it can be synthesised from arginine via the urea cycle in liver, and from glutamine/glutamic acid in the intestinal epithelium. It has a number of beneficial properties including connective tissue strengthening, Stronger Connective Tissue, Decreased Risk Of Heart Disease, Maintenance Of Muscle Tissueand skin health.
Allgemeine Beschreibung
L-Proline is a non-essential amino acid, which is a building block of proteins. Peptides bond to proline, making it a useful building block for proteins. It can be used as a cell culture media component for the commercial biomanufacturing of therapeutic recombinant proteins and monoclonal antibodies. L-Proline plays important roles in various biological processes. It is involved in the synthesis of collagen, which is one of the most abundant proteins in the human body and provides structural support to tissues such as skin, bone, cartilage, and tendons.
Biochem/physiol Actions
Proline is a cyclic, non-essential, hydrophobic amino acid. It is a proteinogenic amino acid which is crucial for primary metabolism. In peptide chains, proline residues confer structural constraints and enhance the susceptibility of proximal peptide bonds to protease activity.
Nebenwirkungen
The only known side effects are reactions from taking too much L-proline, like all amino acids. It causes toxicity levels and amino acid imbalances in your body.
läuterung methode
A likely impurity is hydroxyproline. Purify L-proline via its picrate which is crystallised twice from water, then decomposed with 40% H2SO4. The picric acid is extracted with diethyl ether, the H2SO4 in solution is precipitated with Ba(OH)2, and the filtrate is evaporated. The residue is crystallised from hot absolute EtOH [Mellan & Hoover J Am Chem Soc 73 3879 1951] or EtOH/Et2O. Its solubility in H2O is >100%. It sublimes at 182-187o/0.3mm with 99.4% recovery and unracemised [Gross & Gradsky J Am Chem Soc 77 1678 1955]. It is hygroscopic and is stored in a desiccator. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2178-2199 1961, Beilstein 22 III/IV 8, 22/1 V 31.]
Structure and conformation
L-proline, also known as L-pyrrolidine-2-carboxylic acid, is a neutral amino acid. Although proline is classified as an amino acid, it is strictly speaking an imino acid, since it contains an imino group (carbon-nitrogen double bond). Due to its cyclic pyrrolidine side chain it is classified as a nonpolar aliphatic amino acid.

L-Proline Upstream-Materialien And Downstream Produkte

L-Prolin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

147-85-3, L-Proline Verwandte Suche:

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