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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/REAXYS Number:
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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)
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)
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)
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