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C8754

Sigma-Aldrich

Thiamine pyrophosphate

≥95%, powder

Synonym(s):

Aneurinepyrophosphoric acid, Cocarboxylase, Thiamine pyrophosphate chloride

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About This Item

Empirical Formula (Hill Notation):
C12H19ClN4O7P2S
CAS Number:
154-87-0
Molecular Weight:
460.77
Beilstein:
3875902
EC Number:
205-836-1
MDL number:
MFCD00038740
UNSPSC Code:
12352204
PubChem Substance ID:
24893100
NACRES:
NA.54

product name

Thiamine pyrophosphate, ≥95%

Quality Level

200

Assay

≥95%

form

powder

solubility

H2O: soluble 50 mg/mL, clear to very slightly hazy, colorless

storage temp.

−20°C

SMILES string

CC1=C(CCOP(OP(O)(O)=O)(O)=O)SC=[N+]1CC2=C(N)N=C(C)N=C2.[Cl-]

InChI

1S/C12H18N4O7P2S.ClH/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13;/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21);1H

InChI key

YXVCLPJQTZXJLH-UHFFFAOYSA-N

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Application

Thiamine pyrophosphate from Sigma has been used as a substrate to assay the enzymes in golgi lamellae isolated from rat tissue.
Thiamine pyrophosphate has been used:
  • for the preparation of chitosan nano-particles
  • as a standard for vitamin B1 and its derivative in high-performance
  • liquid chromatography (HPLC) analysis
  • immunofluorescence

Biochem/physiol Actions

Thiamine pyrophosphate (TPP) is a coenzyme of transketolase, that catalyzes the cleavage of ribulose-5-phosphate. This reaction leads to the formation of D-glyceraldehyde-3-phosphate. It requires the addition of an acceptor aldehyde such as ribose-5-phosphate, glyceraldehye or glycolaldehyde. TPP is capable of decarboxylating hydroxypyruvate in the presence of an ′acceptor aldehyde′.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

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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Immunofluorescence Analysis of Human Endocervical Tissue Explants Infected with Neisseria gonorrhoeae
Wang LC, et al.
Bio-protocol, 8(3) (2018)
Effects of anti-CD44 monoclonal antibody IM7 carried with chitosan polylactic acid-coated nano-particles on the treatment of ovarian cancer
Yang Y, et al.
Oncology Letters, 13(1), 99-104 (2017)
Nucleosidediphosphatase activity in the Golgi apparatus and its usefulness for cytological studies.
A B NOVIKOFF et al.
Proceedings of the National Academy of Sciences of the United States of America, 47, 802-810 (1961-06-15)
Thiamine pyrophosphate, a coenzyme of transketolase
Racker E, et al.
Journal of the American Chemical Society, 75(4), 1010-1011 (1953)
Sanshu Li et al.
Nucleic acids research, 41(5), 3022-3031 (2013-02-05)
Thiamin pyrophosphate (TPP) riboswitches are found in organisms from all three domains of life. Examples in bacteria commonly repress gene expression by terminating transcription or by blocking ribosome binding, whereas most eukaryotic TPP riboswitches are predicted to regulate gene expression
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Articles

Thiamine in Cell Culture

How thiamine and other cell culture components affect the performance of serum-free, protein-free cell culture systems used for biomanufacturing heterologous proteins including monoclonal antibodies. The page introduces the in vitro chemistry and biochemistry of thiamine.

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