D-Proline

D-Proline Basic information
Product Name:D-Proline
Synonyms:D-Pro-OH;D-Proline≥ 99% (Assay);D-Proline,99%e.e.;(R)-(+)-PROLINE;(R)-PYRROLIDINE-2-CARBOXYLIC ACID;D-2-PYRROLIDINECARBOXYLIC ACID;D-PYRROLIDINE-2-CARBOXYLIC ACID;D(+)-PROLINE
CAS:344-25-2
MF:C5H9NO2
MW:115.13
EINECS:206-452-7
Product Categories:Amino Acids and Derivatives;Proline [Pro, P];Amino Acids and Derivatives;alpha-Amino Acids;Amino Acids;Biochemistry;Amino ACIDS SERIES;Miscellaneous Biochemicals;Amino Acids & Derivatives;Heterocycles;Isotope Labelled Compounds;206-452-7;bc0001
Mol File:344-25-2.mol
D-Proline Structure
D-Proline Chemical Properties
Melting point 223 °C (dec.) (lit.)
alpha 84.75 º (c=4, H2O)
Boiling point 215.41°C (rough estimate)
density 1.36
refractive index 85 ° (C=4, H2O)
storage temp. Inert atmosphere,Room Temperature
solubility Methanol (Slightly), Water (Sparingly)
pka1.952(at 25℃)
form Powder
color White to yellow to pale brown
optical activity[α]22/D +85.0°, c = 4 in H2O
Water Solubility soluble >1000 g/L (20 ºC)
Sensitive Hygroscopic
BRN 80811
InChIKeyONIBWKKTOPOVIA-SCSAIBSYSA-N
LogP-0.060 (est)
CAS DataBase Reference344-25-2(CAS DataBase Reference)
EPA Substance Registry SystemD-Proline (344-25-2)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 22-36/37/38
Safety Statements 22-24/25-36/37/39-26
WGK Germany 3
3-10
Hazard Note Irritant
TSCA Yes
HS Code 29339990
MSDS Information
ProviderLanguage
D-Pyrrolidine-2-carboxylic acid English
ACROS English
SigmaAldrich English
ALFA English
D-Proline Usage And Synthesis
Chemical PropertiesWhite to off-white powder
OccurrenceD-proline is an isomer of the naturally occurring amino acid, L-Proline. D-amino acids have been found in relatively high abundance in human plasma and saliva. These amino acids may be of bacterial origin, but there is also evidence that they are endogenously produced through amino acid racemase activity.
Usesproline is a skin-conditioning agent. An amino acid found in the collagen molecule.
UsesUsed in the synthesis of (R)-(+)-N-Boc-Pipecolic Acid, (S)-(-)-Coniine, (S)-(+)-Pelletierine, (+)-.beta.-Conhydrine, and (S)-(-)-Ropivacaine and formal synthesis of (-)-Lasubine II and (+)-Cermizine C.
UsesLabelled D-Proline Lasubine II and (+)-Cermizine C.
DefinitionChEBI: D-proline is the D-enantiomer of proline. It has a role as a mouse metabolite. It is a D-alpha-amino acid and a proline. It is a conjugate base of a D-prolinium. It is a conjugate acid of a D-prolinate. It is an enantiomer of a L-proline. It is a tautomer of a D-proline zwitterion.
Synthesis Reference(s)Journal of the American Chemical Society, 71, p. 2818, 1949 DOI: 10.1021/ja01176a065
Tetrahedron Letters, 28, p. 6469, 1987 DOI: 10.1016/S0040-4039(00)96890-4
H-D-PRO-OBZL HCL D-Pyroglutamic acid (2R,4S)-Methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride trans-4-Hydroxy-D-proline H-D-PRO-OTBU TIMTEC-BB SBB003904 AC-D-PRO-OH D-Proline BOC-D-PRO-OSU (3S)-1-(tert-Butoxycarbonyl)-3-pyrrolidinecarboxylic acid TIMTEC-BB SBB004232 cis-4-Hydroxy-D-proline Methyl pyrrolidine-2-carboxylate hydrochloride Ethyl D-(-)-pyroglutamate D-Proline, 4-hydroxy-, methyl ester, hydrochloride (1:1), (4R)- N-Benzyloxycarbonyl-D-proline Z-D-PYR-OH Fmoc-D-proline

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