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250031

Sigma-Aldrich

(R)-(−)-N-(3,5-Dinitrobenzoyl)-α-phenylglycine

99%, for peptide synthesis

Synonym(s):

N-(3,5-Dinitrobenzoyl)-D-α-phenylglycine, R-(−)-N-(3,5-Dinitrobenzoyl)phenylglycine

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About This Item

Linear Formula:
(O2N)2C6H3CONHCH(C6H5)CO2H
CAS Number:
74927-72-3
Molecular Weight:
345.26
Beilstein:
4719763
MDL number:
MFCD00010134
UNSPSC Code:
12352209
PubChem Substance ID:
24855029
NACRES:
NA.22

product name

(R)-(−)-N-(3,5-Dinitrobenzoyl)-α-phenylglycine, 99%

Assay

99%

optical activity

[α]20/D −102°, c = 0.9 in THF

reaction suitability

reaction type: solution phase peptide synthesis

mp

216-217 °C (lit.)

application(s)

peptide synthesis

SMILES string

OC(=O)[C@H](NC(=O)c1cc(cc(c1)[N+]([O-])=O)[N+]([O-])=O)c2ccccc2

InChI

1S/C15H11N3O7/c19-14(16-13(15(20)21)9-4-2-1-3-5-9)10-6-11(17(22)23)8-12(7-10)18(24)25/h1-8,13H,(H,16,19)(H,20,21)/t13-/m1/s1

InChI key

MIVUDAUOXJDARR-CYBMUJFWSA-N

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

Certificates of Analysis (COA)

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Wolfgang Thormann et al.
Journal of pharmaceutical and biomedical analysis, 27(3-4), 555-567 (2002-01-05)
The electrokinetic separation and analysis of the enantiomers of albendazole sulfoxide (ABZSO), a sulfoxide with a sulfur stereogenic center hepatically formed during therapy with the anthelmintic drug albendazole (ABZ), is reported. Using aqueous or nonaqueous alkaline background electrolytes, ABZSO enantiomers
Resolution of enantiomers of 19-hydroxyeicosatetraenoate and 18-hydroxyeicosatetraenoate by chiral phase high-performance liquid chromatography of naphthoyl ester derivatives.
E H Oliw
Journal of chromatography, 526(2), 525-529 (1990-04-06)
S K Yang et al.
Journal of chromatography, 371, 195-209 (1986-12-26)
The direct resolution of K-region cis- and trans-dihydrodiol enantiomers of 14 unsubstituted and methyl- and bromo-substituted benz[a]anthracene (BA) derivatives was investigated by high-performance liquid chromatography with commercially available columns, packed with gamma-aminopropylsilanized silica to which either (R)-N-(3,5-dinitrobenzoyl)phenylglycine (R-DNBPG) or (S)-N-(3,5-dinitrobenzoyl)leucine
Sorin Nita et al.
The journal of physical chemistry. B, 112(41), 13022-13037 (2008-09-25)
A theoretical study of the solvation of ( R)- N-(3,5-dinitrobenzoyl)phenylglycine- and ( R)- N-(3,5-dinitrobenzoyl)leucine-derived chiral stationary phases (CSPs) is presented. Semiflexible models of the chiral selectors are prepared from B3LYP/6-311G** calculations, and these are used in the molecular dynamics simulations
K Roy et al.
Drug design and discovery, 17(4), 315-323 (2002-01-05)
QSAR analyses of matrix metalloproteinase (MMP) inhibitor N-[(substituted phenyl)sulfonyl]-N-4-nitrobenzylglycine hydroxamates, recently reported by Scozzafava and Supuran, have been attempted using linear free energy related (LFER) model of Hansch to explore the contribution patterns of the phenyl ring substitutions (P1' anchoring
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