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19565

Sigma-Aldrich

(6S)-5,6,7,8-Tetrahydro-L-erythro-biopterin sulfate

≥96% (HPLC)

Synonym(s):

(6S)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-4-tetrahydro-(1H)-pteridinone sulfate salt

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About This Item

Empirical Formula (Hill Notation):
C9H15N5O3 · xH2SO4
CAS Number:
109784-74-9
Molecular Weight:
241.25 (free base basis)
MDL number:
MFCD07375456
UNSPSC Code:
12352204
PubChem Substance ID:
329751918
NACRES:
NA.32

Quality Level

100

Assay

≥96% (HPLC)

form

powder or crystals

storage temp.

−20°C

SMILES string

O=C1C2=C(NC[C@]([C@@H](O)[C@@H](O)C)([H])N2)NC(N)=N1.O=S(O)(O)=O

InChI

1S/C9H15N5O3.H2O4S/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7;1-5(2,3)4/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17);(H2,1,2,3,4)/t3-,4-,6-;/m0./s1

InChI key

YCBVHESKFWFUMG-NXYGYYFTSA-N

Biochem/physiol Actions

Important metabolite of the folate biosynthesis pathway. Stereochemistry of biopterin cofactor, tetrahydrobiopterin biosynthesis, regeneration and functions.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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S Matsuura et al.
Journal of biochemistry, 98(5), 1341-1348 (1985-11-01)
The structure of (-)-tetrahydrobiopterin, the cofactor for phenylalanine, tyrosine, and tryptophan hydroxylases, was determined as (6R, 1'R, 2'S)-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin by X-ray crystallographic analysis. The CD spectra of (-)-tetrahydrobiopterin exhibits a negative Cotton effect at 290-240 nm in pH 3.2 solution. The
B Thöny et al.
The Biochemical journal, 347 Pt 1, 1-16 (2000-03-23)
Tetrahydrobiopterin (BH(4)) cofactor is essential for various processes, and is present in probably every cell or tissue of higher organisms. BH(4) is required for various enzyme activities, and for less defined functions at the cellular level. The pathway for the

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