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Merck

250031

(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
NACRES:
NA.22
PubChem Substance ID:
24855029
UNSPSC Code:
12352209
MDL number:
MFCD00010134
Beilstein/REAXYS Number:
4719763

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Product Name

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

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

SMILES string

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

InChI key

MIVUDAUOXJDARR-CYBMUJFWSA-N

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

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1 of 4

This Item
P25485237647190357
(R)-(−)-N-(3,5-Dinitrobenzoyl)-α-phenylglycine 99%

Sigma-Aldrich

250031

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

D−(−)-α-Phenylglycine 99%

Sigma-Aldrich

P25485

D−(−)-α-Phenylglycine

L−(+)-α-Phenylglycine 99%

Sigma-Aldrich

237647

L−(+)-α-Phenylglycine

(R)-(−)-2-Phenylglycinol 98%

Sigma-Aldrich

190357

(R)-(−)-2-Phenylglycinol

assay

99%

assay

99%

assay

99%

assay

98%

optical activity

[α]20/D −102°, c = 0.9 in THF

optical activity

[α]20/D −155°, c = 1 in 1 M HCl

optical activity

[α]20/D +155°, c = 1 in 1 M HCl

optical activity

[α]24/D −31.7°, c = 0.76 in 1 M HCl

mp

216-217 °C (lit.)

mp

302 °C (dec.) (lit.)

mp

>300 °C (lit.)

mp

75-77 °C (lit.)

reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

application(s)

peptide synthesis

application(s)

detection

application(s)

peptide synthesis

application(s)

peptide synthesis

Storage Class

11 - Combustible Solids

wgk

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
BCBQ5443V
BCBQ5446V
BCBQ5440V
1451869V
1451694V

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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)
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
K H Gahm et al.
Analytical chemistry, 67(1), 19-25 (1995-01-01)
Regiospecifically monosubstituted 1-(1-naphthyl)ethylcarbamoylated beta-cyclodextrins (NEC-beta-CDs) were successfully employed as chiral additives in capillary zone electrophoresis (CZE) to achieve chiral separation of N-(3,5-dinitrobenzoyl)phenylglycine (3,5-DNB-PG), phenylalanine (3,5-DNB-PA), and homophenylalanine (3,5-DNB-HPA). The enantioselectivity of the various site-substituted NEC-beta-CDs in CZE was compared with
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
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