D-Glutamine
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D-Glutamine
structure -
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CAS No:
5959-95-5
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Formula:
C5H10N2O3
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Chemical Name:
D-Glutamine
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Synonyms:
D-Glutamine;Glutamine,D-;(2R)-2-Amino-4-carbamoylbutanoic acid;(2R)-5-Amino-2-azaniumyl-5-oxopentanoate;(R)-2,5-Diamino-5-oxopentanoic acid
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CAS No:
Description
D-Glutamine is a cell-permeable D type stereoisomer of Glutamine.
Solid
D-glutamine is the D-enantiomer of glutamine. It has a role as a mouse metabolite. It is a D-alpha-amino acid and a glutamine. It is a conjugate base of a D-glutaminium. It is a conjugate acid of a D-glutaminate. It is an enantiomer of a L-glutamine. It is a tautomer of a D-glutamine zwitterion.|A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from glutamic acid and ammonia. It is the principal carrier of nitrogen in the body and is an important energy source for many cells.|A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.
Characteristics
106.41000
-3.1
Solid
1.321 g/cm3
184-185 °C
445.6ºC at 760 mmHg
223.3ºC
1.564
42.53g/L(temperature not stated)
-15ºC
Safety Information
NONH for all modes of transport
3
R36/37/38
S26-S36/37/39
Xi
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
D-Glutamine Use and Manufacturing
5-(2, 6-dioxopiperidin-3-yl)-5H-thieno(3, 4-c)pyrrole-4, 6-dione (Method 1) To a 250 mL round bottom flask equipped with an electromagnetic stirrer, 14.6 g of glutamine, 60 mL of water, and 60 mL of TFA were added. When glutamine fully dissolved, the reaction mixture was cooled on an ice bath to between 0 and 5C, and 15.4 g of theino(3, 4-c)furan-1, 3-dione was added. At the above temperature, the reaction mixture was allowed to react for 30 min. The reaction mixture was then allowed to warm to room temperature and allowed to react for additional 4h. The reaction mixture was stripped of solvent in vacuo at 85C over 4h to obtain a tacky solid (28 g). The solid was dissolved in 140 mL of anhydrous THF, and 20 g of CDI and a catalytic quantity of DMAP were added and allowed to react at a reflux for 6h untill a large amount of white solid precipitated. The white solid was cooled and filtered to yield 18 g of dried title compound. 1H NMR (DMSO-d6): delta 11.10 (s, 1H), 8.26 (s, 2H), 5.03 (dd, 1H, J = 3Hz, J = 3Hz), 2.87-2.82 (m, 1H), 2.66-2.55 (m, 2H), 2.07-2.04 (m, 1H); MS (m/z): 263 (M-1)+.
D-Glutamine is an unnatural isomer of L-Glutamine that is present in human plasma an is a source of liberated ammonia. D-Glutamine can be synthesized by enzymatic means or can be found in cheeses, wine and vinegars as well. It is often used to determine the activity of Glutamine synthetase, an enzyme that is commonly found in the mammalian liver and brain that controls the use of nitrogen in cells.
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Computed Properties
Molecular Weight:146.14
XLogP3:-3.1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:146.06914219
Monoisotopic Mass:146.06914219
Topological Polar Surface Area:106
Heavy Atom Count:10
Complexity:146
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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