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58689

Supelco

N-Isobutyryl-D-cysteine

for chiral derivatization, LiChropur™, ≥97.0%

Synonym(s):

N-(2-Methylpropionyl)-D-cysteine

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About This Item

Linear Formula:
HSCH2CH[NHCOCH(CH3)2]CO2H
CAS Number:
124529-07-3
Molecular Weight:
191.25
MDL number:
MFCD00155641
UNSPSC Code:
12000000
eCl@ss:
32160406
PubChem Substance ID:
329758446
NACRES:
NA.22

grade

for chiral derivatization

Quality Level

100

product line

ChiraSelect™

assay

≥97.0% (RT)
≥97.0%

form

solid

optical purity

enantiomeric ratio: ≥99.5:0.5 (HPLC)

quality

LiChropur™

mp

97-101 °C (lit.)
97-101 °C

storage temp.

2-8°C

SMILES string

CC(C)C(=O)N[C@H](CS)C(O)=O

InChI

1S/C7H13NO3S/c1-4(2)6(9)8-5(3-12)7(10)11/h4-5,12H,3H2,1-2H3,(H,8,9)(H,10,11)/t5-/m1/s1

InChI key

BWBQXMAXLAHHTK-RXMQYKEDSA-N

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General description

It was used for derivatization of amino acid mixtures of OPA during HPLC analysis of L- and D-amino acids in plants.[1]
N-Isobutyryl-D-cysteine is a chiral thiol mostly used in precolumn orthophthaldehyde (OPA) derivatization of amino acids.[2]

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Legal Information

ChiraSelect is a trademark of Sigma-Aldrich Co. LLC
LiChropur is a trademark of Merck KGaA, Darmstadt, Germany

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCBS2528V

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Chromatographic determination of L- and D-amino acids in plants.
Bruckner H and Westhauser T.
Amino Acids, 24 (1-2), 43-55 (2003)
Handbook of HPLC
Danilo Corradini
Science, 715-715 (2011)
Hui Gan et al.
Angewandte Chemie (International ed. in English), 48(29), 5282-5286 (2009-03-25)
The right fit: Plasmid DNA molecules show chirality-dependent interaction with gold surfaces modified by L and D N-isobutyrylcysteine. Relaxed DNA molecules have a stronger interaction and adsorption on the L surface, while their counterparts on the D surface maintain a
Stereospecific interaction between immune cells and chiral surfaces.
Taolei Sun et al.
Journal of the American Chemical Society, 129(6), 1496-1497 (2007-02-08)
H Brückner et al.
Journal of chromatography. A, 711(1), 201-215 (1995-09-08)
In order to evaluate and extend the applicability of an analytical method that enables the quantitative and simultaneous high-performance liquid chromatographic determination of D- and L-amino acids (DL-AAs) by automated precolumn derivatization with o-phthaldialdehyde together with the chiral thiol N-isobutyryl-L-cysteine
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