CAS 79206-51-2

(2R,3R,4R,5S)-3,4,5-Trihydroxy-2-(hydroxymethyl)-1-piperidinehexanoic acid

Description:

The chemical substance known as (2R,3R,4R,5S)-3,4,5-Trihydroxy-2-(hydroxymethyl)-1-piperidinehexanoic acid, with the CAS number 79206-51-2, is a complex organic compound characterized by its piperidine ring structure, which is a six-membered ring containing one nitrogen atom. This compound features multiple hydroxyl (-OH) groups, specifically three hydroxyl groups at the 3, 4, and 5 positions, contributing to its hydrophilicity and potential for forming hydrogen bonds. The presence of a hydroxymethyl group at the 2 position further enhances its solubility in polar solvents. The stereochemistry indicated by the (2R,3R,4R,5S) configuration suggests specific spatial arrangements of the substituents, which can influence the compound's biological activity and interactions. This substance may exhibit properties relevant to pharmaceutical applications, particularly in the context of drug design and development, due to its structural features that can interact with biological targets. Its unique characteristics make it a subject of interest in medicinal chemistry and related fields.

Formula: C₁₂H₂₃NO₆

InChI: InChI=1S/C12H23NO6/c14-7-8-11(18)12(19)9(15)6-13(8)5-3-1-2-4-10(16)17/h8-9,11-12,14-15,18-19H,1-7H2,(H,16,17)/t8-,9+,11-,12-/m1/s1

InChI key: InChIKey=KTNVTDIFZTZBJY-RBLKWDMZSA-N

SMILES: C(CCCCC(O)=O)N1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1

Synonyms:

• 1-Piperidinehexanoic acid, 3,4,5-trihydroxy-2-(hydroxymethyl)-, (2R,3R,4R,5S)-
• N-5-Carboxypentyl-1-deoxynojirimycin
• (2R,3R,4R,5S)-3,4,5-Trihydroxy-2-(hydroxymethyl)-1-piperidinehexanoic acid
• 1-Piperidinehexanoic acid, 3,4,5-trihydroxy-2-(hydroxymethyl)-, [2R-(2α,3β,4α,5β)]-

N-5-Carboxypentyl-1-deoxynojirimycin

CAS: 79206-51-2

Molecular weight: 277.31

Ref: 7W-GC4982

6-[(2R,3R,4R,5S)-2-(Hydroxymethyl)-3,4,5-trihydroxypiperidin-1-yl]hexanoic acid

CAS: 79206-51-2

6-[(2R,3R,4R,5S)-2-(Hydroxymethyl)-3,4,5-trihydroxypiperidin-1-yl]hexanoic acid

Purity: ≥95%

Molecular weight: 277.31g/mol

Ref: 54-OR8120T

N-5-Carboxypentyl-1-deoxynojirimycin

Controlled Product

CAS: 79206-51-2

Applications Ligand used for the preparation of an affinity resin highly specific for glucosidase I purification. Glucosidase I is involved in the post-translational processing of N-linked glycoproteins.
References HettKamp, H., et al.: Eur. J. Biochem., 142, 85 (1984); Shailubhai, K., et al.: Biochem. J., 247, 555 (1987); Bause, E., et al.: FEBS, 278, 167 (1991)

Formula: C₁₂H₂₃NO₆

Color and Shape: Off White Crystalline

Molecular weight: 277.31

Ref: TR-C181200

N-(5-Carboxypentyl)-deoxynojirimycin

CAS: 79206-51-2

N-(5-Carboxypentyl)-deoxynojirimycin is a synthetic glycosylation agent that is used in the preparation of oligosaccharides, polysaccharides and saccharide complexes. This compound is also a potential therapeutic agent for cancer, as it can inhibit tumor cell growth by inhibiting protein synthesis. N-(5-Carboxypentyl)-deoxynojirimycin can be used as an intermediate in the synthesis of other fluorinated sugars. When modified with methyl groups, this compound has shown anticancer activity against human breast cancer cells.

Formula: C₁₂H₂₃NO₆

Purity: Min. 95 Area-%

Color and Shape: Beige Powder

Molecular weight: 277.31 g/mol

Ref: 3D-MC04528

N-5-Carboxypentyl-1-deoxynojirimycin

CAS: 79206-51-2

1-Deoxynojirimycin, a potent glucose analog, inhibits α-glucosidase I and II effectively. Its derivative, N-5-Carboxypentyl-1-deoxynojirimycin, serves as a ligand for glucosidase I and II purification, utilizing carboxypentyl groups for affinity chromatography resin linkage. Furthermore, N-5-Carboxypentyl-1-deoxynojirimycin demonstrates comparable or superior inhibition of glucosidase compared to 1-deoxynojirimycin, with inhibition constants (Ki) of 0.45 µM and 2.1 µM, respectively, for pig liver glucosidase I.

Formula: C₁₂H₂₃NO₆

Color and Shape: Solid

Molecular weight: 277.317

Ref: TM-T84411