D-alpha-phenylglycine (CHEBI:44962)

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CHEBI:44962 - D-α-phenylglycine

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ChEBI Name	D-α-phenylglycine

ChEBI ID	CHEBI:44962

ChEBI ASCII Name	D-alpha-phenylglycine

Definition	The R stereoisomer of α-phenylglycine.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:439820, CHEBI:44959, CHEBI:44925

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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20 20 0 0 0 0 999 V2000

-1.3500 1.5720 1.1380 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.0280 0.1690 0.8440 C 0 0 2 0 0 0 0 0 0 0 0 0

0.4030 0.0690 0.3820 C 0 0 0 0 0 0 0 0 0 0 0 0

0.9240 1.0270 -0.4670 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2380 0.9370 -0.8880 C 0 0 0 0 0 0 0 0 0 0 0 0

3.0280 -0.1160 -0.4660 C 0 0 0 0 0 0 0 0 0 0 0 0

2.5050 -1.0770 0.3790 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1930 -0.9850 0.8030 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.9430 -0.3400 -0.2400 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.5140 0.4410 -0.9640 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.1230 -1.6600 -0.4010 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.6520 1.9000 1.7880 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2130 2.0870 0.2810 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1620 -0.4310 1.7440 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7100 -1.9870 -1.0970 H 0 0 0 0 0 0 0 0 0 0 0 0

0.7840 -1.7360 1.4630 H 0 0 0 0 0 0 0 0 0 0 0 0

3.1220 -1.9000 0.7080 H 0 0 0 0 0 0 0 0 0 0 0 0

4.0530 -0.1880 -0.7970 H 0 0 0 0 0 0 0 0 0 0 0 0

2.6460 1.6880 -1.5480 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3070 1.8500 -0.7970 H 0 0 0 0 0 0 0 0 0 0 0 0

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2 9 1 0 0 0 0

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3 8 4 0 0 0 0

4 5 4 0 0 0 0

4 20 1 0 0 0 0

5 6 4 0 0 0 0

5 19 1 0 0 0 0

6 7 4 0 0 0 0

6 18 1 0 0 0 0

7 8 4 0 0 0 0

7 17 1 0 0 0 0

8 16 1 0 0 0 0

9 10 2 0 0 0 0

9 11 1 0 0 0 0

11 15 1 0 0 0 0

M END): 22 ms

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Formula

C8H9NO2

Net Charge

Average Mass

151.165

Monoisotopic Mass

151.06333

InChI

InChI=1S/C8H9NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,9H2,(H,10,11)/t7-/m1/s1

InChIKey

ZGUNAGUHMKGQNY-SSDOTTSWSA-N

SMILES

C(=O)([C@H](N)C=1C=CC=CC1)O

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via alpha-phenylglycine )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	D-α-phenylglycine (CHEBI:44962) is a α-phenylglycine (CHEBI:55484) D-α-phenylglycine (CHEBI:44962) is enantiomer of L-α-phenylglycine (CHEBI:439819) D-α-phenylglycine (CHEBI:44962) is tautomer of D-α-phenylglycine zwitterion (CHEBI:77399)

Incoming	N-carbamoyl-D-phenylglycine (CHEBI:141249) has functional parent D-α-phenylglycine (CHEBI:44962) N-carbamoyl-D-phenylglycine(1−) (CHEBI:140758) has functional parent D-α-phenylglycine (CHEBI:44962) L-α-phenylglycine (CHEBI:439819) is enantiomer of D-α-phenylglycine (CHEBI:44962) D-α-phenylglycine zwitterion (CHEBI:77399) is tautomer of D-α-phenylglycine (CHEBI:44962)

IUPAC Name

(2R)-amino(phenyl)acetic acid

Synonyms	Sources
(R)-phenylglycine	ChEMBL
D-(-)-alpha-Phenylglycine	ChemIDplus
D-PHENYLGLYCINE	PDBeChem

Manual Xref	Database
PG9	PDBeChem
View more database links

Registry Numbers	Types	Sources
2208676	Beilstein Registry Number	Beilstein
364514	Gmelin Registry Number	Gmelin
875-74-1	CAS Registry Number	ChemIDplus

Citations

Wang CL, Fan YB, Lu HH, Tsai TH, Tsai MC, Wang HP (2010)
Evidence of D-phenylglycine as delivering tool for improving L-dopa absorption.
Journal of biomedical science 17, 71 [PubMed:20815935]
[show Abstract]

Background

L-dopa has been used for Parkinson's disease management for a long time. However, its wide variety in the rate and the extent of absorption remained challenge in designing suitable therapeutic regime. We report here a design of using D-phenylglycine to guard L-dopa for better absorption in the intestine via intestinal peptide transporter I (PepT1).

Methods

D-phenylglycine was chemically attached on L-dopa to form D-phenylglycine-L-dopa as a dipeptide prodrug of L-dopa. The cross-membrane transport of this dipeptide and L-dopa via PepT1 was compared in brush-boarder membrane vesicle (BBMV) prepared from rat intestine. The intestinal absorption was compared by in situ jejunal perfusion in rats. The pharmacokinetics after i.v. and p.o. administration of both compounds were also compared in Wistar rats. The striatal dopamine released after i.v. administration of D-phenylglycine-L-dopa was collected by brain microdialysis and monitored by HPLC. Anti-Parkinsonism effect was determined by counting the rotation of 6-OHDA-treated unilateral striatal lesioned rats elicited rotation with (+)-methamphetamine (MA).

Results

The BBMV uptake of D-phenylglycine-L-dopa was inhibited by Gly-Pro, Gly-Phe and cephradine, the typical PepT1 substrates, but not by amino acids Phe or L-dopa. The cross-membrane permeability (Pm*) determined in rat jejunal perfusion of D-phenylglycine-L-dopa was higher than that of L-dopa (2.58 ± 0.14 vs. 0.94 ± 0.10). The oral bioavailability of D-phenylglycine-L-dopa was 31.7 times higher than that of L-dopa in rats. A sustained releasing profile of striatal dopamine was demonstrated after i. v. injection of D-phenylglycine-L-dopa (50 mg/kg), indicated that D-phenylglycine-L-dopa might be a prodrug of dopamine. D-phenylglycine-L-dopa was more efficient than L-dopa in lowering the rotation of unilateral striatal lesioned rats (19.1 ± 1.7% vs. 9.9 ± 1.4%).

Conclusion

The BBMV uptake studies indicated that D-phenylglycine facilitated the transport of L-dopa through the intestinal PepT1 transporter. The higher jejunal permeability and the improved systemic bioavailability of D-phenylglycine-L-dopa in comparison to that of l-dopa suggested that D-phenylglycine is an effective delivery tool for improving the oral absorption of drugs like L-dopa with unsatisfactory pharmacokinetics. The gradual release of dopamine in brain striatum rendered this dipeptide as a potential dopamine sustained-releasing prodrug.

Mayorga C, Obispo T, Jimeno L, Blanca M, Moscoso del Prado J, Carreira J, Garcia JJ, Juarez C (1995)
Epitope mapping of beta-lactam antibiotics with the use of monoclonal antibodies.
Toxicology 97, 225-234 [PubMed:7716788]
[show Abstract]

Last Modified

25 November 2019

CHEBI:44962 - D-α-phenylglycine

Background

Methods

Results

Conclusion

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