13-Hydroxylupanine

• CAS: 15358-48-2
• Catalog Number: ACM15358482
• Category: Other Products
• Molecular Weight: 264.36
• Molecular Formula: C₁₅H₂₄N₂O₂
• Synonyms: (+)-13α-Hydroxylupanine hydrochloride
• InChI: InChI=1S/C15H24N2O2/c18-12-4-5-16-8-10-6-11(14(16)7-12)9-17-13(10)2-1-3-15(17)19/h10-14,18H,1-9H2
• InChI Key: JVYKIBAJVKEZSQ-UHFFFAOYSA-N
• Melting Point: 169-170 °C
• Complexity: 386
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 0
• Exact Mass: 264.183778013
• Heavy Atom Count: 19
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• Monoisotopic Mass: 264.183778013
• Physical State: Powder
• Rotatable Bond Count: 0
• Topological Polar Surface Area: 43.8 Ų

Case Study

13-Hydroxylupanine in the Biosynthesis of Quinolizidine Alkaloids

Wink M. Journal of chemical ecology, 2019, 45(2), 109-115.

Quinolizidines (QAs) are an important class of alkaloids that have been extensively studied as defense chemicals in plants. The biosynthetic process of QA involves the following important aspects:
· The process of QA biosynthesis begins with the amino acid lysine, which is decarboxylated by lysine decarboxylase (LDC) to form the diamine cadaverine.
· Cadaverine is then desaminated either by a transaminase or an oxidase to produce 5-aminopentanal. Through a complex reaction, the amino group of 5-aminopentanal reacts with the aldehyde function of two additional molecules of 5-aminopentanal to form a tetracyclic quinolizidine ring skeleton, which can be further converted into sparteine or lupanine.
· Hydroxylation of lupanine to 13-hydroxylupanine allows for the generation of ester alkaloids by tigloyl-CoA: 13-hydroxylupanine O-tigloyl transferase.
· Methyl groups can be transferred to free nitrogen atoms in certain QA molecules, such as cytisine, by S-adenosyl-Lmethionine: N-methyltransferase.
· Genes for LDC, cadaverine oxidase, and tigloyl-CoA: 13-hydroxylupanine O- tigloyl transferase have been discovered. Currently, the transcriptomes of QA-producing plants are being analyzed using RNASeq to discover additional genes involved in QA synthesis, storage, and transport.

Custom Q&A

What is the chemical formula for 13-hydroxylupanine?

The chemical formula for 13-hydroxylupanine is C15H24N2O2.

What is the molecular weight of 13-hydroxylupanine?

The molecular weight of 13-hydroxylupanine is 264.36.

What is the melting point of 13-hydroxylupanine?

The melting point of 13-hydroxylupanine is 169-170°C.

In what solvents is 13-hydroxylupanine slightly soluble?

13-hydroxylupanine is slightly soluble in chloroform and methanol.

What is the specific rotation of 13-hydroxylupanine in ethanol and water?

The specific rotation of 13-hydroxylupanine in ethanol is +45.6° and in water is +65.1°.

What is the storage temperature recommended for 13-hydroxylupanine?

The recommended storage temperature for 13-hydroxylupanine is -20°C in a freezer under an inert atmosphere.

What is the usage of (+)-13α-Hydroxylupanine in analytical studies?

(+)-13α-Hydroxylupanine is used in analytical studies for the determination of Lupinus polyphyllus by thin-layer chromatography and fluorescence.

What is the pKa value of 13-hydroxylupanine?

The pKa value of 13-hydroxylupanine is 14.82±0.20 (predicted).

What color is 13-hydroxylupanine in its solid form?

13-hydroxylupanine is off-white to pale yellow in color in its solid form.

What is the primary function of hydroxylupanine as an alkaloid?

Hydroxylupanine is an inhibitor of ganglionic transmission as an alkaloid found in L. lanatus.