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858919

Sigma-Aldrich

D-Proline

≥99%, for peptide synthesis, ReagentPlus®

Synonym(s):

(R)-Pyrrolidine-2-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C5H9NO2
CAS Number:
344-25-2
Molecular Weight:
115.13
Beilstein:
80811
EC Number:
206-452-7
MDL number:
MFCD00064317
UNSPSC Code:
12352209
PubChem Substance ID:
24888479
NACRES:
NA.22

product name

D-Proline, ReagentPlus®, ≥99%

product line

ReagentPlus®

Assay

≥99%

form

powder

optical activity

[α]22/D +85.0°, c = 4 in H2O

optical purity

ee: 98% (GLC)

reaction suitability

reaction type: solution phase peptide synthesis

mp

223 °C (dec.) (lit.)

application(s)

peptide synthesis

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.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Total Synthesis of the Securinega Alkaloid (−)-Secu?amamine A.
Liu P, et al.
Journal of the American Chemical Society, 130(24), 7562-7563 (2008)
Michael Meanwell et al.
Science (New York, N.Y.), 369(6504), 725-730 (2020-08-09)
Nucleoside analogs are commonly used in the treatment of cancer and viral infections. Their syntheses benefit from decades of research but are often protracted, unamenable to diversification, and reliant on a limited pool of chiral carbohydrate starting materials. We present
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)
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)
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