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D7006

Sigma-Aldrich

Dihydrofolic acid

≥90%

Synonym(s):

7,8-Dihydropteroyl-L-glutamic acid, Dihydropteroyl-L-glutamic acid, FAH2

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About This Item

Empirical Formula (Hill Notation):
C19H21N7O6
CAS Number:
4033-27-6
Molecular Weight:
443.41
Beilstein:
69017
MDL number:
MFCD00083619
UNSPSC Code:
12352106
PubChem Substance ID:
24894068
NACRES:
NA.79

biological source

synthetic (organic)

Quality Level

200

Assay

≥90%

form

powder

color

light yellow to dark yellow-orange

storage temp.

−20°C

SMILES string

NC1=NC(=O)C2=C(NCC(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=N2)N1

InChI

1S/C19H21N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1

InChI key

OZRNSSUDZOLUSN-LBPRGKRZSA-N

Gene Information

human ... DHFRP1(573971)
mouse ... Dhfr(13361)

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General description

Intermediate in mammalian conversion of dietary folic acid to tetrahydrofolate by dihydrofolate reductase (DHFR). In bacteria, dihydrofolic acid is generated from 7,8-dihydropteroate by dihydrofolate synthetase.

Application

Dihydrofolic acid has been used in diaphorase-coupled assay for dihydrofolate reductase (DHFR) activity. It has also been used as a component in assay buffer to determine dihydrofolate reductase (DHFR) activity.

Biochem/physiol Actions

Folic acid (FA) and dihydrofolic acid (FAH2) are substrates of dihydrofolate reductase(s) which reduce them to tetrahydrofolate (THF), which in turn supports ‘one carbon′ transfer. Tetrahydrofolates are required for de novo synthesis of purines, thymidylic acid and various amino acids and for post-translational methylation (epigenetics).

Packaging

Sealed ampule.

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Pricing

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Karunesh Arora et al.
Journal of the American Chemical Society, 131(15), 5642-5647 (2009-03-28)
Conformational changes in enzymes are well recognized to play an important role in the organization of the reactive groups for efficient catalysis. This study reveals atomic and energetic details of the conformational change process that precedes the catalytic reaction of
Nina M Antikainen et al.
Biochemistry, 44(51), 16835-16843 (2005-12-21)
Ensemble kinetics and single-molecule fluorescence microscopy were used to study conformational transitions associated with enzyme catalysis by dihydrofolate reductase (DHFR). The active site loop of DHFR was labeled with a fluorescence quencher, QSY35, at amino acid position 17, and the
Z Attias et al.
Endocrine-related cancer, 13(2), 571-581 (2006-05-27)
The insulin-like growth factor-I receptor (IGF-IR) has an important role in colorectal cancer development and progression. IGF-IR displays a potent anti-apoptotic activity and is overexpressed in primary tumors and colon cancer-derived cell lines. Folic acid, a member of the vitamin
T Yoshikawa et al.
Biotechnology and bioengineering, 74(5), 435-442 (2001-06-28)
In previous work, we clarified the relationship between the productivity and stability of gene-amplified cells and the location of the amplified gene. The location of the amplified gene enabled us to classify resistant cells into two types. One type of
Sri Rama Koti Ainavarapu et al.
Biophysical journal, 89(5), 3337-3344 (2005-08-16)
We use single-molecule force spectroscopy to demonstrate that the mechanical stability of the enzyme dihydrofolate reductase (DHFR) is modulated by ligand binding. In the absence of bound ligands, DHFR extends at very low forces, averaging 27 pN, without any characteristic
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