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Details

Stereochemistry ABSOLUTE
Molecular Formula C5H10N2O3
Molecular Weight 146.1445
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of D-GLUTAMINE

SMILES

N[C@H](CCC(N)=O)C(O)=O

InChI

InChIKey=ZDXPYRJPNDTMRX-GSVOUGTGSA-N
InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m1/s1

HIDE SMILES / InChI

Molecular Formula C5H10N2O3
Molecular Weight 146.1445
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

D-glutamine is an unnatural D type stereoisomer of glutamine which is one of the 20 amino acids encoded by the standard genetic code.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Influence of d-glutamine and d-glutamic acid sequences in optical peptide probes targeted against the cholecystokinin-2/gastrin-receptor on binding affinity, specificity and pharmacokinetic properties.
2013-11-15
Proposal of protocols using D-glutamine to optimize the 2,3-bis(2-methoxy-4-nitro-5-sulfophenly)-5-[(phenylamino)carbonyl]-2H-tetrazolium hydroxide (XTT) assay for indirect estimation of microbial loads in biofilms of medical importance.
2011-02
Effects of glutamine isomers on human (Caco-2) intestinal epithelial proliferation, strain-responsiveness, and differentiation.
2000-11-04
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
It was evaluated the effects of the interaction between mechanical strain and glutamine supplementation in human Caco-2 intestinal epithelial cells, and pursued the finding of equivalent effects of L- and D-glutamine in Caco-2, HT-29, and primary malignant human colonocytes. Caco-2 cells were subjected to repetitive strain in media containing 2 mmol/L of L-glutamine and media supplemented with L- or D-glutamine. Deformation at 10 cpm and L-glutamine supplementation from 2 to 5 mmol/L concentrations independently stimulated Caco-2 proliferation; the combination further increased proliferation. D-Glutamine supplementation yielded similar results, although with lesser potency. Furthermore, both L- and D-glutamine equivalently reduced Caco-2 dipeptidyl dipeptidase activity. The effects of each isoform were blocked by 1 to 3 mmol/L acivicin, a selective antagonist of glutamine metabolism.
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:21:23 GMT 2025
Edited
by admin
on Mon Mar 31 22:21:23 GMT 2025
Record UNII
63HB36CA2Y
Record Status Validated (UNII)
Record Version
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Name Type Language
D-GLUTAMINE
Systematic Name English
GLUTAMINE, D-
Preferred Name English
Code System Code Type Description
PUBCHEM
145815
Created by admin on Mon Mar 31 22:21:23 GMT 2025 , Edited by admin on Mon Mar 31 22:21:23 GMT 2025
PRIMARY
FDA UNII
63HB36CA2Y
Created by admin on Mon Mar 31 22:21:23 GMT 2025 , Edited by admin on Mon Mar 31 22:21:23 GMT 2025
PRIMARY
CHEBI
58000
Created by admin on Mon Mar 31 22:21:23 GMT 2025 , Edited by admin on Mon Mar 31 22:21:23 GMT 2025
PRIMARY
DRUG BANK
DB02174
Created by admin on Mon Mar 31 22:21:23 GMT 2025 , Edited by admin on Mon Mar 31 22:21:23 GMT 2025
PRIMARY
CAS
5959-95-5
Created by admin on Mon Mar 31 22:21:23 GMT 2025 , Edited by admin on Mon Mar 31 22:21:23 GMT 2025
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CHEBI
48097
Created by admin on Mon Mar 31 22:21:23 GMT 2025 , Edited by admin on Mon Mar 31 22:21:23 GMT 2025
PRIMARY
CHEBI
17061
Created by admin on Mon Mar 31 22:21:23 GMT 2025 , Edited by admin on Mon Mar 31 22:21:23 GMT 2025
PRIMARY
EPA CompTox
DTXSID6046345
Created by admin on Mon Mar 31 22:21:23 GMT 2025 , Edited by admin on Mon Mar 31 22:21:23 GMT 2025
PRIMARY