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P45850

Sigma-Aldrich

Pipecolinic acid

98%, for peptide synthesis

Synonym(s):

(±)-Piperidine-2-carboxylic acid, 2-Piperidinecarboxylic acid, Homoproline, Pipecolic acid free base

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About This Item

Empirical Formula (Hill Notation):
C6H11NO2
CAS Number:
535-75-1
Molecular Weight:
129.16
Beilstein:
81095
EC Number:
208-616-3
MDL number:
MFCD00064347
UNSPSC Code:
12352106
PubChem Substance ID:
24898555
NACRES:
NA.22

product name

Pipecolinic acid, 98%

Assay

98%

form

powder and chunks

reaction suitability

reaction type: solution phase peptide synthesis

technique(s)

LC/MS: suitable

color

white to beige

mp

282 °C (dec.) (lit.)

SMILES string

OC(=O)C1CCCCN1

InChI

1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)

InChI key

HXEACLLIILLPRG-UHFFFAOYSA-N

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General description

Pipecolinic acid also known as 2-piperidinecarboxylic acid, is a versatile reagent used in the solution phase peptide synthesis. It has been commonly utilized as a replacement for proline in many peptidomimetic syntheses.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBK7655
STBK4086
STBK1151
STBJ7170
STBJ3981

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Conformational heterogeneity about pipecolic acid peptide bonds: conformational, thermodynamic, and kinetic aspects
WJ Wu, et.al.
The Journal of Organic Chemistry, 63, 6689-6698 (1998)
D M Danks et al.
The Journal of pediatrics, 86(3), 382-387 (1975-03-01)
Studies of eight patients with this syndrome confirm the characteristic pattern of abnormalities and the autosomal recessive mode of inheritance. The incidence is estimated to be approximately 1 in 100,000 live births. The liver lesion proved to be variable, with
B Plecko et al.
Annals of neurology, 48(1), 121-125 (2000-07-14)
Diagnosis of pyridoxine-dependent epilepsy is based on the clinical response to high-dosage application of pyridoxine. Here, we report on 2 patients with pyridoxine-dependent epilepsy with significant elevation of pipecolic acid concentrations in plasma and cerebrospinal fluid (CSF) and further increase
J Greter et al.
Clinical chemistry, 29(3), 434-437 (1983-03-01)
The urine of two patients with Refsum's disease consistently contained 2,6-dimethyloctanedioic acid, a compound not normally found in human urine. In addition, their urines contained increased concentrations of 3-methylhexanedioic acid. These two compounds may be formed from phytanic acid by
Isabelle M Medana et al.
The Journal of infectious diseases, 185(5), 650-656 (2002-02-28)
A retrospective study of 261 Vietnamese adults with severe malaria was conducted to determine the relationship between cerebrospinal fluid (CSF) levels of metabolites of the kynurenine pathway, the incidence of neurologic complications, and the disease outcome. Three metabolites were measured:
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Chromatograms

application for HPLC

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