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670871

Sigma-Aldrich

(S)-(+)-Pyrrolidine-3-carboxylic acid

≥98.0% (NT)

Synonym(s):

(S)-β-Proline

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About This Item

Empirical Formula (Hill Notation):
C5H9NO2
CAS Number:
72580-53-1
Molecular Weight:
115.13
Beilstein:
3537293
MDL number:
MFCD06738463
UNSPSC Code:
12352106
PubChem Substance ID:
329760393
NACRES:
NA.22

Assay

≥98.0% (NT)

form

solid

optical activity

[α]/D 20.0±2.0°, c = 2 in H2O

reaction suitability

reaction type: solution phase peptide synthesis

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

OC(=O)[C@H]1CCNC1

InChI

1S/C5H9NO2/c7-5(8)4-1-2-6-3-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1

InChI key

JAEIBKXSIXOLOL-BYPYZUCNSA-N

Related Categories

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

670871-VAR:
670871-500MG:
670871-BULK:

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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Santi Spampinato et al.
European journal of pharmacology, 469(1-3), 89-95 (2003-06-05)
We previously described a novel endomorphin-1 analogue (Tyr-L-beta-Pro-Trp-Phe-NH(2); Endo1-beta-Pro) more resistant to enzymatic hydrolysis than endomorphin-1 that acts as a mu-opioid receptor agonist. In this study we report that Endo1-beta-Pro, s.c. injected in the mouse, is an effective antinociceptive agent
Souvik Banerjee et al.
The Journal of organic chemistry, 77(23), 10925-10930 (2012-11-07)
A straightforward stereoselective and enantiodivergent cyclization strategy for the construction of γ-lactams is described. The cyclization strategy makes use of chiral malonic esters prepared from enantiomerically enriched monoesters of disubstituted malonic acid. The cyclization occurs with the selective displacement of
Cody Timmons et al.
The Journal of organic chemistry, 70(19), 7634-7639 (2005-09-10)
[reaction: see text] A new halo-Mannich-type reaction is reported using cyclopropyl carbonyl-derived enolates and sulfonyl-protected imines. Chiral oxazolidinones auxiliaries were found to be effective for completely controlling the stereochemistry of the products. Variations in the oxazolidinone, protecting group, and imine
Alan Armstrong et al.
The Journal of organic chemistry, 74(14), 5041-5048 (2009-06-03)
7-Azabicyclo[2.2.1]heptane-2-carboxylic acid 11 was prepared in enantiopure form, and its catalytic potential in the direct aldol reaction between acetone and 4-nitrobenzaldehyde was assessed. The bicyclic system was found to be more selective than its monocyclic analogue beta-proline 5b. A comparative
Haile Zhang et al.
Journal of the American Chemical Society, 130(3), 875-886 (2008-01-01)
The development of enantioselective anti-selective Mannich-type reactions of aldehydes and ketones with imines catalyzed by 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives is reported in detail. Both (3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid and (R)-3-pyrrolidinecarboxylic acid efficiently catalyzed the reactions of aldehydes with alpha-imino esters
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