858919

Sigma-Aldrich

D-Proline

ReagentPlus®, ≥99%

Sinónimos:
(R)-Pyrrolidine-2-carboxylic acid
Empirical Formula (Hill Notation):
C5H9NO2
Número de CAS:
Peso molecular:
115.13
Beilstein/REAXYS Number:
80811
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

product line

ReagentPlus®

assay

≥99%

optical activity

[α]22/D +85.0°, c = 4 in H2O

optical purity

ee: 98% (GLC)

reaction suitability

reaction type: solution phase peptide synthesis

application(s)

peptide synthesis: suitable

mp

223 °C (dec.) (lit.)

SMILES string

OC(=O)[C@H]1CCCN1

InChI

1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1

InChI key

ONIBWKKTOPOVIA-SCSAIBSYSA-N

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Application

D-Proline is a key starting material in the total synthesis of (−)-secu′amamine A and (R)-harmicine.
  • It can be used as a ligand for the synthesis of chiral polyoxometalate (POM) clusters.
  • It can also be used as a catalyst in the enantioselective α-aminoxylation of aldehydes.

Packaging

5 g in glass bottle
500 mg in glass bottle

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 858919.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificado de Análisis

Certificado de origen

A Facile and Rapid Route to Highly Enantiopure 1, 2?Diols by Novel Catalytic Asymmetric α?Aminoxylation of Aldehydes.
Zhong G
Angewandte Chemie (International Edition in English), 115(35), 4379-4382 (2003)
Chiral 3D architectures with helical channels constructed from polyoxometalate clusters and copper?amino acid complexes.
An H Y, et al.
Angewandte Chemie (International Edition in English), 118(6), 918-922 (2006)
Total Synthesis of the Securinega Alkaloid (−)-Secu?amamine A.
Liu P, et al.
Journal of the American Chemical Society, 130(24), 7562-7563 (2008)
Christian Dank et al.
Molecules (Basel, Switzerland), 25(3) (2020-01-25)
The synthesis of the alkaloid (-)-monophyllidin is described. The molecule is a hybrid of xanthoxyline and (S)-proline, accessible in one-step through a Mannich reaction. In the solid-state, defined structural arrangements with different physical properties are formed. Single crystal X-ray diffraction...
Synthesis of (S)?and (R)?Harmicine from Proline: An Approach Toward Tetrahydro?β?carbolines.
Lood C S and Koskinen A M
European Journal of Organic Chemistry, 2014(11), 2357-2364 (2014)

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