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670774

Sigma-Aldrich

(R)-(−)-Pyrrolidine-3-carboxylic acid

≥99.0% (NT)

Synonym(s):

(R)-β-Proline

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About This Item

Empirical Formula (Hill Notation):
C5H9NO2
CAS Number:
72580-54-2
Molecular Weight:
115.13
Beilstein:
5496144
MDL number:
MFCD08272856
UNSPSC Code:
12352200
PubChem Substance ID:
329760387

Assay

≥99.0% (NT)

form

solid

optical activity

[α]/D -20.5±1.5°, 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-/m1/s1

InChI key

JAEIBKXSIXOLOL-SCSAIBSYSA-N

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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

670774-BULK:
670774-VAR:
670774-1G:
670774-250MG:

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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Sigma-Aldrich

P0380

L-Proline

B R Huck et al.
Organic letters, 1(11), 1717-1720 (2000-06-03)
[formula: see text] Homooligomers of beta-amino acids (S)-3-pyrrolidine-3-carboxylic acid (PCA) and (S)-nipecotic acid (Nip) were studied by circular dichroism (CD) in methanol. In each series, a profound change in the far-UV CD spectrum was observed from monomer to tetramer, but
G Johnson et al.
Journal of medicinal chemistry, 35(2), 233-241 (1992-01-24)
3-Carboxy-3,4-dehydropyrrolidine was found to bind with affinity equal to that of glycine in a [3H]strychnine binding assay. Simple substitution of the 1-, 2-, 4-, or 5-position resulted in marked loss of affinity. A decline in affinity was also found upon
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
Giuliana Cardillo et al.
Journal of medicinal chemistry, 45(12), 2571-2578 (2002-05-31)
In this paper we describe the synthesis and affinity toward the mu-opioid receptor of some tetrapeptides obtained from endomorphin-1, H-Tyr-Pro-Trp-Phe-NH(2) (1), by substituting each amino acid in turn with its homologue. The ability to bind mu-opioid receptors depends on the
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
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