124-20-9

Basic information

• Product Name: Spermidine
• Synonyms: 1,8-DIAMINO-4-AZAOCTANE;SPERMIDINE FREE BASE;SPERMIDINE;OMEGA-AMINOBUTYL-OMEGA-AMINOPROPYLAMINE;N1-(3-AMINOPROPYL)BUTANE-1,4-DIAMINE;N-(3-AMINOPROPYL)-1,4-BUTANDIAMINE;N-[3-AMINOPROPYL]-1,4-BUTANEDIAMINE;N-(3-AMINOPROPYL)-1,4-DIAMINOBUTANE
• CAS NO: 124-20-9
• Molecular Formula: C₇H₁₉N₃
• Molecular Weight: 145.25
• EINECS: 204-689-0
• Product Categories: co-factor
• Mol File: 124-20-9.mol
• Article Data: 20

Chemical Properties

• Melting Point: 23-25 °C
• Boiling Point: 128-130 °C (14 mmHg)
• Flash Point: >230 °F
• Appearance: Clear colorless/Liquid After Melting
• Density: 1.00 g/mL at 20 °C
• Vapor Pressure: 0.0269mmHg at 25°C
• Refractive Index: n20/D 1.479(lit.)
• Storage Temp.: 2-8°C
• Solubility: H2O: 1 M at 20 °C, clear, colorless
• PKA: 10.53±0.19(Predicted)
• Water Solubility: Miscible with water, ethanol and ether.
• Sensitive: Air Sensitive
• Stability: Stable, but air-sensitive and very hygroscopic - store under argon. Incompatible with acids, acid chlorides, acid anhydrides, ox
• Merck: 14,8742
• BRN: 1698591
• CAS DataBase Reference: Spermidine(CAS DataBase Reference)
• NIST Chemistry Reference: Spermidine(124-20-9)
• EPA Substance Registry System: Spermidine(124-20-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-27
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 3
• RTECS: EJ7000000
• F: 3-10-34
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 124-20-9(Hazardous Substances Data)

Usage

Description

Spermidine is an endogenous polyamine. It is formed from putrescine by spermidine synthase.

Chemical Properties

Spermidine solution is a colorless clear liquid with very hygroscopic and oxidizable. It is soluble in water (50 mg/ml), ethanol, and ether.

Source

Spermidine is found in fresh green pepper, wheat germ, cauliflower, broccoli, mushrooms, and a variety of cheeses. Even higher amounts are found in soybean products such as natto, shitake mushrooms, amaranth grain and durian. Some of these ingredients are particularly common in a Mediterranean diet, which may explain why some believe eating like the Spanish can prolong your life.

Uses

Spermidine can be used in electroporation while transferring the DNA into the cell under the electrical impulse. May be used for purification of DNA-binding proteins. Spermidine is also used, along with calcium chloride, for precipitating DNA onto microprojectiles for bombardment with a gene gun.

Application

Spermidine serves as a precursor of spermine and essential for both normal and neoplastic tissue growth. It was first detected in human sperm, but occurs widely in nature. It is essential in both normal and neoplastic tissue growth. Spermidine has a role in cell growth processes and the formation and interconversion of spermidine in mammalian cells has been reported. It has been studied in the regulation of tRNA methyltransferase activity and stimulates T4 polynucleotide kinase activity.

Definition

ChEBI: Spermidine is a triamine that is the 1,5,10-triaza derivative of decane. It is a polyamine that is routinely included in restriction enzyme digestions to improve the cleavage efficacy of the DNA. Spermidine counteracts the inhibitory effects of contaminants coisolated with DNA and consequently permits complete digestion of the DNA at lower enzyme concentrations.

Preparation

The linker resin 2 was used in the synthesis of spermidine. In order to initiate the preparation the 2-nitrossulfonamide was anchored on the resin 2 by reaction in THF under reflux. The resulting resin 3 then reacted with 4-bromobutylphthalimide in acetonitrile in the presence of Cs2CO3 as base, generating the resin 4. Protected spermidine 5 was cleaved from resin 4 after treatment with hydrate hydrazine at room temperature. Spermidine 5 was previously prepared by our group in solution system utilizing Fukuyama's sulfonamide.Synthesis and Characterization of a Linker for Primary Amines used in the Solid Phase Organic Synthesis of SpermidineJ. Braz. Chem. Soc., Vol. 22, No. 1, 86-91, 2011DOI: 10.1590/S0103-50532011000100011

Mode of action

Spermidine's main mechanism of action is its ability to induce autophagy, a self-preservation process which clears out toxic, damaged and dysfunctional cells, resulting in lower levels of inflammation in the body. Autophagy is the main mechanism of spermidine in delaying aging and prolonging the lifespan. In addition, spermidine exerts its effects through other mechanisms, including anti-inflammation, histone acetylation reduction, lipid metabolism and regulation of cell growth and signaling pathways.

References

Madeo, F., Eisenberg, T., Pietrocola, F., et al. Spermidine in health and disease. Science 359(6374), eaan2788 (2018).Lopatin, A.N., Makhina, E.N., and Nichols, C.G. Potassium channel block by cytoplasmic polyamines as the mechanism of intrinsic rectification. Nature 372(6504), 366-369 (1994).Eisenberg, T., Knauer, H., Schauer, A., et al. Induction of autophagy by spermidine promotes longevity. Nat. Cell Biol. 11(11), 1305-1314 (2009).Guo, X., Harada, C., Namekata, K., et al. Spermidine alleviates severity of murine experimental autoimmune encephalomyelitis. Invest. Ophthalmol. Vis. Sci. 52(5), 2696-2703 (2011).Eisenberg, T., Abdellatif, M., Schroeder, S., et al. Cardioprotection and lifespan extension by the natural polyamine spermidine. Nat. Med. 22(12), 1428-1438 (2016).

InChI:InChI=1/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2/p+3

Synthetic route

4-aza-1,3-bis(1,3-dibenzylhexahydro-2-oxo-1,3,5-triazin-5-yl)octane (143565-69-9) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9)

Conditions	Yield
With piperidine In methanol at 65℃;	90%

[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-carbamic acid tert-butyl ester (177085-34-6) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9)

Conditions	Yield
With hydrazine hydrate In ethanol at 60℃; for 12h;	45%

N-(3-bromo-propyl)-butanediyldiamine → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9)

Conditions	Yield
With ammonia

4-(2-cyano-ethylamino)-butyronitrile; hydrochloride → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9)

Conditions	Yield
With hydrogenchloride; platinum Hydrogenation;

N8-acetylspermidine dihydrochloride (34450-15-2, 120205-19-8) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9)

Conditions	Yield
With hydrogenchloride

N-(cyanoethyl)-1,4-diaminobutane (4748-73-6) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9)

Conditions	Yield
With ammonia; hydrogen; nickel In ethanol

Spermine (71-44-3) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + Trimethylenediamine (109-76-2)

Conditions	Yield
With pyrroloquinoline quinone In water at 37℃; examination of PQQ oxidation effect; phosphate buffer (pH=7.2);

Spermine (71-44-3) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + 1,4-diaminobutane (110-60-1) + acrolein (107-02-8)

Conditions	Yield
With phosphate buffer In water at 37℃; Product distribution; bovine serum amine oxidase; other polyamines;

kinetin (525-79-1) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + Spermine (71-44-3) + 1,4-diaminobutane (110-60-1)

Conditions	Yield
at 30℃; for 24h; effect on poliamine content and ratio in rice embryos of Oryza sativa;

(R)-(-)-abscisic acid (14398-53-9) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + Spermine (71-44-3) + 1,4-diaminobutane (110-60-1)

Conditions	Yield
at 30℃; for 24h; effect on poliamine content and ratio in rice embryos of Oryza sativa;

N1,N5-di-(E)-coumaroyl-spermidine (114916-04-0) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + para-coumaric acid (7400-08-0)

Conditions	Yield
With hydrogenchloride at 100℃; for 4h;
With sodium hydroxide at 100℃; for 4h;

N5,N10-di-(E,E)-feruloylspermidine → 3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + N-(3-aminopropyl)-1,4-diaminobutane (124-20-9)

Conditions	Yield
With sodium hydroxide at 100℃; for 4h;
With hydrogenchloride at 100℃; for 4h;

tetrahydroperiphylline (64482-04-8) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9)

Conditions	Yield
With potassium hydroxide Heating;

Spermine (71-44-3) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + propionaldehyde (123-38-6) + Trimethylenediamine (109-76-2)

Conditions	Yield
With NaPi buffer; oxygen at 37℃; for 0.166667h; catalase and polyamine oxidase presence, pH 6.5, other polyamines and acetylpolyamines, kinetic constants Km (μM) and Vmax (μmol H2O2 formed μg protein-1 min-1);

1-amino-4-<γ-bromo-propylamino>-butane → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9)

Conditions	Yield
With ethanol; ammonia at 100℃;

N-(3-benzylaminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine (1111644-29-1) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + N-ethyl-1,3-diaminopropane (10563-23-2) + N-benzyl-1,3-diaminopropane (13910-48-0) + N-(3-aminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine + benzylamine (100-46-9) + N1-(3-ethylaminopropyl)butane-1,4-diamine + N-{3-[(4-aminobutyl)amino]propyl}(phenylmethyl)amine

Conditions	Yield
With spermine oxidase pH=9.5; Kinetics; pH-value; Reagent/catalyst; Enzymatic reaction;

N-(3-aminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9)

Conditions	Yield
With spermine oxidase pH=9.5; Kinetics; pH-value; Reagent/catalyst; Enzymatic reaction;

N-(3-aminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + Spermine (71-44-3) + N-ethyl-1,3-diaminopropane (10563-23-2) + N1-(3-ethylaminopropyl)butane-1,4-diamine

Conditions	Yield
With recombinant human polyamine oxidase pH=9.5; Kinetics; pH-value; Reagent/catalyst; Enzymatic reaction;

N(1)-(3-(ethylamino)propyl)butane-1,4-diamine trihydrochloride → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + N-ethyl-1,3-diaminopropane (10563-23-2) + 1,4-diaminobutane (110-60-1)

Conditions	Yield
With recombinant human polyamine oxidase pH=9.5; Kinetics; pH-value; Reagent/catalyst; Enzymatic reaction;

N1-(3-aminopropyl)-N4-(3-(benzylamino)propyl)butane-1,4-diamine → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + Spermine (71-44-3) + benzylamine (100-46-9) + N-{3-[(4-aminobutyl)amino]propyl}(phenylmethyl)amine

Conditions	Yield
With recombinant human polyamine oxidase pH=9.5; Kinetics; pH-value; Reagent/catalyst; Enzymatic reaction;

N1-(3-aminopropyl)-N4-(3-(benzylamino)propyl)butane-1,4-diamine → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + benzylamine (100-46-9)

Conditions	Yield
With spermine oxidase pH=9.5; Kinetics; pH-value; Reagent/catalyst; Enzymatic reaction;

N-{3-[(4-aminobutyl)amino]propyl}(phenylmethyl)amine → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + N-benzyl-1,3-diaminopropane (13910-48-0) + 1,4-diaminobutane (110-60-1)

Conditions	Yield
With spermine oxidase pH=9.5; Kinetics; pH-value; Reagent/catalyst; Enzymatic reaction;

N-{3-[(4-aminobutyl)amino]propyl}(phenylmethyl)amine → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + 1,4-diaminobutane (110-60-1)

Conditions	Yield
With recombinant human polyamine oxidase pH=9.5; Kinetics; pH-value; Reagent/catalyst; Enzymatic reaction;

Spermine (71-44-3) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + 3-aminopropanal (352-92-1)

Conditions	Yield
Stage #1: Spermine With recombinant human flavin-dependent spermine oxidase at 25℃; for 0.00166667h; pH=8.3; aq. buffer; Inert atmosphere; Enzymatic reaction; Stage #2: With oxygen at 25℃; pH=8.3; Kinetics; Mechanism; pH-value; Time; aq. buffer; Enzymatic reaction;
With recombinant mouse spermine oxidase at 25℃; pH=8.5; Kinetics; Reagent/catalyst; aq. phosphate buffer;
With Saccharomyces cerevisiae recombinant polyamine oxidase Fms1; water; oxygen at 25℃; pH=9.35; Kinetics; Reagent/catalyst; Concentration; Enzymatic reaction;

glutathionylspermidine disulfide → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + GLUTATHIONE (70-18-8)

Conditions	Yield
With glutathionylspermidine synthetase/amidase; GSH reductase; water; NADP at 25℃; pH=7.3; aq. buffer; Enzymatic reaction;

N-(3-benzylaminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine (1111644-29-1) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: spermine oxidase / pH 9.5 / Enzymatic reaction 2: spermine oxidase / pH 9.5 / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: recombinant human polyamine oxidase / pH 9.5 / Enzymatic reaction 2: spermine oxidase / pH 9.5 / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: spermine oxidase / pH 9.5 / Enzymatic reaction 2: recombinant human polyamine oxidase / pH 9.5 / Enzymatic reaction View Scheme

N-(3-benzylaminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine (1111644-29-1) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + Spermine (71-44-3) + N-ethyl-1,3-diaminopropane (10563-23-2) + N1-(3-ethylaminopropyl)butane-1,4-diamine

Conditions	Yield
Multi-step reaction with 2 steps 1: spermine oxidase / pH 9.5 / Enzymatic reaction 2: recombinant human polyamine oxidase / pH 9.5 / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: recombinant human polyamine oxidase / pH 9.5 / Enzymatic reaction 2: recombinant human polyamine oxidase / pH 9.5 / Enzymatic reaction View Scheme

N-(3-benzylaminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine (1111644-29-1) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + N-benzyl-1,3-diaminopropane (13910-48-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: spermine oxidase / pH 9.5 / Enzymatic reaction 2: spermine oxidase / pH 9.5 / Enzymatic reaction View Scheme

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → N1,N8-bis(tert-butoxycarbonyl)spermidine (83392-10-3)

Conditions	Yield
In tetrahydrofuran at 0℃; for 1h;	100%
In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;	95%
In tetrahydrofuran for 1h;	86%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + 2,3-dimethoxybenzoic acid (1521-38-6) → N1,N8-Bis(2,3-bis(methyloxy)benzoyl)spermidine (78217-75-1)

Conditions	Yield
With 1,1'-carbonyldiimidazole In dichloromethane	100%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + 1,1'-carbonyldiimidazole (530-62-1) + tert-butyl alcohol (75-65-0) → N1,N8-bis(tert-butoxycarbonyl)spermidine (83392-10-3)

Conditions	Yield
Stage #1: 1,1'-carbonyldiimidazole; tert-butyl alcohol With potassium hydroxide In toluene at 60℃; for 3h; Inert atmosphere; Stage #2: N-(3-aminopropyl)-1,4-diaminobutane In toluene at 60℃; for 3h; Inert atmosphere;	100%
Stage #1: 1,1'-carbonyldiimidazole; tert-butyl alcohol With potassium hydroxide In toluene at 60℃; for 3h; Stage #2: N-(3-aminopropyl)-1,4-diaminobutane In toluene at 60℃; for 3h;	20.22 g

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + benzyl cyanoformate (5532-86-5) → <3-<<4-(carboxyamino)butyl>amino>propyl>carbamic acid, dibenzyl ester (89965-56-0)

Conditions	Yield
In dichloromethane at 20℃; for 3h;	99%
In dichloromethane at 0℃; for 2h;	95%
In chloroform at 23℃; for 16h;	71%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + N-tetradecanoyl-L-proline → C45H85N5O4

Conditions	Yield
Stage #1: N-tetradecanoyl-L-proline With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 20℃; for 1.5h; Stage #2: N-(3-aminopropyl)-1,4-diaminobutane In dichloromethane for 20h;	99%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + 5-benzoyl-3-(cyclopent-1-en-1-yl)-5-phenyl-1,5-dihydro-4H-pyrazol-4-one → N1,N8-bis(benzoyl)spermidine (73038-07-0)

Conditions	Yield
In dichloromethane at 20℃; for 24h; regioselective reaction;	98%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + acetaldehyde (75-07-0) → 1-<4'-(N-ethylidene)aminobutyl>-2-methylhexahydropyrimidine (82995-34-4)

Conditions	Yield
In chloroform at 5 - 10℃; for 0.0833333h;	97%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + (2E)-but-2-enedioic acid (110-17-8) → spermidine fumarate

Conditions	Yield
In water for 0.25h;	97%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + 2-phenyl-2,3-dihydro[1]benzofuro[2,3-e][1,2,4]triazin-3-one (202266-40-8) → 1,5,10-tris[6-(2-hydroxyphenyl)-3-oxo-2-phenyl-1,2,4-triazin-5-yl]-1,5,10-triazadecane

Conditions	Yield
In chloroform at 50℃; for 18h;	96.3%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + N-ethoxycarbonylphthalimide (22509-74-6) → N1,N10-bisphthaloylspermidine (104435-58-7)

Conditions	Yield
In dichloromethane at 20℃; for 2.5h;	96%
In dichloromethane at 25℃; for 2h;	90%
In chloroform at 20 - 25℃; for 0.75h;	75%
at 20 - 25℃;
In chloroform Acylation;

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + ethyl trifluoroacetate, (383-63-1) → N1,N8-bis(trifluoroacetyl)spermidinetriamine trifluoacetate

Conditions	Yield
With water In acetonitrile Heating;	96%
In water; acetonitrile Heating;	92%
With water In acetonitrile for 7h;	89%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + 2-acetyldimedone (1755-15-3) → N(1),N(8)-bis[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-spermidine (193334-87-1)

Conditions	Yield
With triethylamine In ethanol for 8h; Heating;	96%

formaldehyd (50-00-0) + N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) → 1-(4-aminobutyl)-1,2,3,4,5,6-hexahydropyrimidine (73453-98-2)

Conditions	Yield
	95%
In water at 20℃; for 1h;	94%
In water for 1h;	91%

N,N'-di-t-butyloxycarbonyl-(S)-lysine N-hydroxysuccinimide ester (30189-36-7) + N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) → (5-{3-[4-(2,6-bis-tert-butoxycarbonylamino-hexanoylamino)-butylamino]-propylcarbamoyl}-5-tert-butoxycarbonylamino-pentyl)-carbamic acid tert-butyl ester

Conditions	Yield
With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 24h;	95%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + (S)-4,5-dihydro-2-(3-hydroxy-2-pyridinyl)-4-methyl-4-thiazolecarboxylic acid (76045-30-2) → N1,N8-bis(desferrithiocinoyl) spermidine (133817-93-3)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 15h; Ambient temperature;	93%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + acetonitrile (75-05-8) → N1,N3-spermidinebis(acetamide) (82414-35-5)

Conditions	Yield
With water; dihydridotetrakis(triphenylphosphine)ruthenium In 1,2-dimethoxyethane at 160℃; for 24h;	93%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + poly(3-acyl-2-oxazolone)((R=Me) → N1,N3-spermidinebis(acetamide) (82414-35-5)

Conditions	Yield
In tetrahydrofuran for 6h; Ambient temperature;	93%

benzoyl cyanide (613-90-1) + N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) → N1,N8-bis(benzoyl)spermidine (73038-07-0)

Conditions	Yield
In dichloromethane at 20℃; for 3h;	92%
In dichloromethane for 15h; Ambient temperature;	92%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + (3E)-2-oxo-4-phenylbutenenitrile (6047-90-1) → N1,N8-dicinnamoyl spermidine (41590-65-2)

Conditions	Yield
In dichloromethane at 20℃; for 3h;	92%
In dichloromethane for 15h; Ambient temperature;	92%
In dichloromethane Ambient temperature;	92%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + ethyl trifluoroacetate, (383-63-1) → N-[4-(trifluoroacetamido)butyl]-N-[3-(trifluoroacetamido)propyl]amine (158474-89-6)

Conditions	Yield
In water; acetonitrile for 12h; Heating;	92%
With water In acetonitrile for 7h; Heating;	89%
With water In acetonitrile Heating;

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + hexachlorocyclotriphosphazene (N3P3Cl6) → (2,4,4,6,6-Pentachloro-2λ5,4λ5,6λ5-[1,3,5,2,4,6]triazatriphosphinin-2-yl)-[4-(2,2,4,4-tetrachloro-1,3,5,7,11-pentaaza-2λ5,4λ5,6λ5-triphospha-spiro[5.5]undeca-1(6),2,4-trien-7-yl)-butyl]-amine (90510-43-3)

Conditions	Yield
With triethylamine In diethyl ether; hexane for 96h; Ambient temperature;	91.6%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + trifluoroacetic anhydride (407-25-0) → tris(trifluoroacetyl)spermidine (65372-69-2)

Conditions	Yield
With pyridine for 0.25h; Ambient temperature;	91.1%
With pyridine

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + 3-(2,2'-dimethoxybiphenyl)-3-carbonyl-1,3-thiazolidine-2-thione (156660-01-4) → C37H43N3O6 (156660-02-5)

Conditions	Yield
In dichloromethane for 12h; Ambient temperature;	91%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) → C7H16Cl3N3P3

Conditions	Yield
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In chloroform for 48h; Ambient temperature;	90.7%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + N-acetyl-N-(2-isopropyl-4-oxo-4H-quinazolin-3-yl)acetamide (178244-37-6) → N1,N3-spermidinebis(acetamide) (82414-35-5) + 3-acetylamino-2-isopropylquinazolin-4(3H)-one (144522-58-7)

Conditions	Yield
In dichloromethane	A n/a B 90%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + [(3aR,4S,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-dithioacetic acid methyl ester (207276-64-0) → 1-N,8-N-bis[2-C-(2,3:5,6-di-O-isopropylidene)-β-D-mannofuranosylethanethioyl]spermidine

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 24h;	90%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + 8-bromocaffeine (10381-82-5) → 8-(4-(3-aminopropylamino)-butylamino)caffeine

Conditions	Yield
In ethanol for 26h; Reflux;	90%
In ethanol

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + 1,10-Bis-(2-thioxo-thiazolidin-3-yl)-decane-1,10-dione (74058-85-8) → 1,5,10-Triaza-cycloicosane-11,20-dione (74059-41-9)

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	89%

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) → 1-hydroxy-2-oxo-3-(3-aminopropyl)-3-(4-aminobutyl)-1-triazene

Conditions	Yield
With nitrogen(II) oxide In acetonitrile under 3800 Torr; for 23h; Ambient temperature;	88%

Upstream product

• 114916-04-0 N¹,N⁵-di-(E)-coumaroyl-spermidine 
• 103493-34-1 [4-(3-aminopropylamino)butyl]carbamic acid tert-butyl ester 
• 64482-04-8 tetrahydroperiphylline 
• 334-50-9 spermidine trihydrochloride 
• 177085-34-6 [4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-carbamic acid tert-butyl ester 
• 25593-72-0 N₁-acetylspermine 
• 61345-84-4 N₁,N₁₂-diethylspermine 
• 117654-79-2 1,14-bis(phenylmethyl)-1,5,10,14-tetraazatetradecane tetrahydrochloride 
• 1111644-29-1 N-(3-benzylaminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine 
• 108081-77-2 glutathionylspermidine disulfide 
• 71-44-3 Spermine 
• 143565-69-9 4-aza-1,3-bis(1,3-dibenzylhexahydro-2-oxo-1,3,5-triazin-5-yl)octane 
• 14398-53-9 (R)-(-)-abscisic acid 
• 525-79-1 kinetin 

Downstream Products

• 73038-07-0 N¹,N⁸-bis(benzoyl)spermidine 
• 58478-34-5 N-<3-(9-acridinylamino)propyl>-N-<4-(9-acridinylamino)butyl>amine 
• 41590-65-2 N¹,N⁸-dicinnamoyl spermidine 
• 89965-56-0 <3-<<4-(carboxyamino)butyl>amino>propyl>carbamic acid, dibenzyl ester 
• 83392-10-3 N¹,N⁸-bis(tert-butoxycarbonyl)spermidine 
• 89647-71-2 N¹,N⁸-bis(3,4-dimethoxybenzoyl)spermidine 
• 75956-66-0 N,N',N'',N'''-tris<2,3-dimethoxy-4-(carbomethoxy)benzoyl>-1,5,10-triazadecane 
• 130203-31-5 N-[(S)-1-[4-(3-Amino-propylamino)-butylcarbamoyl]-2-(4-benzyloxy-phenyl)-ethyl]-butyramide 
• 131928-10-4 5-Hydroxy-3-[1-(4-hydroxy-phenyl)-meth-(E)-ylidene]-3H-benzofuran-2-one; compound with N¹-(3-amino-propyl)-butane-1,4-diamine 
• 89647-69-8 N¹,N⁸-bis(2,3-hydroxybenzoyl)spermidine 
• 101330-61-4 di-(E)-feruloylspermidine 
• 74272-81-4 2,3-bis(benzyloxy)-N-(3-(4-(2,3-bis(benzyloxy)benzamido)butylamino)propyl)benzamide 
• 99520-38-4 C₅₇H₅₉N₁₁O₁₄ 
• 143209-07-8 1,5,10-tris<<2-(2'-hydroxyphenyl)-2-thiazolin-4-yl>carbonyl>-1,5,10-triazadecane 

Related news

Corrosion inhibition performance of Spermidine (cas 124-20-9) on mild steel in acid media09/28/2019

The corrosion inhibition and adsorption behavior of spermidine on mild steel (MS) in 1 M sulfuric and 0.50 M hydrochloric acid have been investigated at room temperature by electrochemical methods viz., electrochemical impedance spectroscopy (EIS) and Tafel polarization techniques. The adsorptio...detailed

Effect of Spermidine (cas 124-20-9) and D-arginine treatments on ethylene synthesis in Xinjiang ‘Saimaiti’ apricot10/01/2019

Xinjiang ‘Saimaiti’ apricots in the green ripe stage were used as the experimental materials. The apricots were treated with spermidine (Spd) and d-arginine (D-Arg). Fruit firmness, ethylene production, 1-aminocyclopropane-1-carboxylic-acid (ACC) synthase activity, ACC oxidase activity and gen...detailed

Spermidine (cas 124-20-9) influences enhanced micropropagation and antibacterial activity in Aerva javanica (Burm. F.) Shult.09/27/2019

Aerva javanica is an exotic medicinal plant widely distributed in India. It possesses numerous medicinal benefits. The present study was aimed to in vitro regenerate the explants of Aerva javanica, and to quantify the components of secondary metabolites (using high performance liquid chromatogra...detailed

Polyamine oxidase 2 is involved in regulating excess Spermidine (cas 124-20-9) contents during seed germination and early seedling development in Arabidopsis thaliana09/26/2019

To understand the physiological functions of polyamine oxidases (PAOs) in plants, we analyzed the effects of exogenous polyamines during seed germination and early seedling development, using Arabidopsis thaliana lines independently harboring T-DNA insertions in each PAO gene. Spermine caused se...detailed

Spermidine (cas 124-20-9) ameliorates the neuronal aging by improving the mitochondrial function in vitro09/25/2019

Changes in mitochondrial structure and function are the initial factors of cell aging. Spermidine has an antiaging effect, but its effect on neuronal aging and mitochondrial mechanisms is unclear. In this study, mouse neuroblastoma (N2a) cells were treated with d‑galactose (d‑Gal) to establish c...detailed

Spermidine (cas 124-20-9) induced aggregation of terphenyl derivative: An efficient probe for detection of Spermidine (cas 124-20-9) in living cells09/24/2019

A terphenyl derivative 3 has been designed and synthesized which undergoes self-assembly in mixed aqueous media to form weakly emissive aggregates. Aggregates of derivative 3 selectively detect spermidine and exhibit spermidine-induced emission enhancement. The interactions between aggregates of...detailed

Helicobacter pylori does not use Spermidine (cas 124-20-9) synthase to produce Spermidine (cas 124-20-9)09/10/2019

Helicobacter pylori is the primary pathogen associated to gastritis and gastric cancer. Growth of H. pylori depends on the availability of spermidine in vivo. Interestingly, the genome of H. pylori contains an incomplete set of genes for the classical pathway of spermidine biosynthesis. It is th...detailed

Cardioprotection by Spermidine (cas 124-20-9) does not depend on structural characteristics of the myocardial microcirculation in aged mice09/09/2019

AimsAgeing is associated with cardiovascular disease and reduced cardiac function. This cardiac functional decline is accompanied by cardiac remodeling and alterations in cardiomyocyte composition. Recently, it was shown that the natural polyamine spermidine preserves cardiac function and cardio...detailed

Spectroscopic and molecular docking studies on the interaction between Spermidine (cas 124-20-9) and pancreatic elastase09/08/2019

In this study, the impact of spermidine on the stability, conformation and activity of elastase was investigated at the pH of 8.5 (the optimum pH for elastase) and different temperatures (303, 313, and 323 K) using UV–vis spectrophotometry, Spectrofluorimetry, circular dichroism, and enzyme act...detailed

Relevant articles and documents

Probing mammalian spermine oxidase enzyme-substrate complex through molecular modeling, site-directed mutagenesis and biochemical characterization

Spermine oxidase (SMO) and acetylpolyamine oxidase (APAO) are FAD-dependent enzymes that are involved in the highly regulated pathways of polyamine biosynthesis and degradation. Polyamine content is strictly related to cell growth, and dysfunctions in polyamine metabolism have been linked with cancer. Specific inhibitors of SMO and APAO would allow analyzing the precise role of these enzymes in polyamine metabolism and related pathologies. However, none of the available polyamine oxidase inhibitors displays the desired characteristics of selective affinity and specificity. In addition, repeated efforts to obtain structural details at the atomic level on these two enzymes have all failed. In the present study, in an effort to better understand structure-function relationships, SMO enzyme-substrate complex has been probed through a combination of molecular modeling, site-directed mutagenesis and biochemical studies. Results obtained indicate that SMO binds spermine in a similar conformation as that observed in the yeast polyamine oxidase FMS1-spermine complex and demonstrate a major role for residues His82 and Lys367 in substrate binding and catalysis. In addition, the SMO enzyme-substrate complex highlights the presence of an active site pocket with highly polar characteristics, which may explain the different substrate specificity of SMO with respect to APAO and provide the basis for the design of specific inhibitors for SMO and APAO.

Mechanistic and structural analyses of the roles of active site residues in yeast polyamine oxidase Fms1: Characterization of the N195A and D94N enzymes

Flavoprotein Fms1 from Saccharomyces cerevisiae catalyzes the oxidation of spermine in the biosynthetic pathway for pantothenic acid. The same reaction is catalyzed by the mammalian polyamine and spermine oxidases. The active site of Fms1 contains three amino acid residues positioned to interact with the polyamine substrate, His67, Asn195, and Asp94. These three residues form a hydrogen-bonding triad with Asn195 being the central residue. Previous studies of the effects of mutating His67 are consistent with that residue being important both for interacting with the substrate and for maintaining the hydrogen bonds in the triad [Adachi, M. S., Taylor, A. B., Hart, P. J., and Fitzpatrick, P. F. (2012) Biochemistry 51, 4888-4897]. The N195A and D94N enzymes have now been characterized to evaluate their roles in catalysis. Both mutations primarily affect the reductive half-reaction. With N 1-acetylspermine as the substrate, the rate constant for flavin reduction decreases ～450-fold for both mutations; the effects with spermine as the substrate are smaller, 20-40-fold. The kcat/Kamine- and kcat-pH profiles with N1-acetylspermine are only slightly changed from the profiles for the wild-type enzyme, consistent with the pKa values arising from the amine substrate or product and not from active site residues. The structure of the N195A enzyme was determined at a resolution of 2.0 ?. The structure shows a molecule of tetraethylene glycol in the active site and establishes that the mutation has no effect on the protein structure. Overall, the results are consistent with the role of Asn195 and Asp94 being to properly position the polyamine substrate for oxidation.

A lysine conserved in the monoamine oxidase family is involved in oxidation of the reduced flavin in mouse polyamine oxidase

Lysine 315 of mouse polyamine amine oxidase corresponds to a lysine residue that is conserved in the flavoprotein amine oxidases of the monoamine oxidase structural family. In several structures, this lysine residue forms a hydrogen bond to a water molecule that is hydrogen-bonded to the flavin N(5). Mutation of Lys315 in polyamine oxidase to methionine was previously shown to have no effect on the kinetics of the reductive half-reaction of the enzyme (M. Henderson Pozzi, V. Gawandi, P.F. Fitzpatrick, Biochemistry 48 (2009) 1508-1516). In contrast, the mutation does affect steps in the oxidative half-reaction. The kcat value is unaffected by the mutation; this kinetic parameter likely reflects product release. At pH 10, the kcat/Km value for oxygen is 25-fold lower in the mutant enzyme. The kcat/KO2 value is pH-dependent for the wild-type enzyme, decreasing below a pKa of 7.0, while this kinetic parameter for the mutant enzyme is pH-independent. This is consistent with the neutral form of Lys315 being required for more rapid flavin oxidation. The solvent isotope effect on the kcat/KO2 value increases from 1.4 in the wild-type enzyme to 1.9 in the mutant protein, and the solvent inventory changes from linear to bowed. The effects of the mutation can be explained by the lysine orienting the bridging water so that it can accept the proton from the flavin N(5) during flavin oxidation. In the mutant enzyme the lysine amine would be replaced by a water chain.

Preparation method of spermidine

The invention relates to the technical field of preparation of compounds, in particular to a preparation method of spermidine. The method comprises the following steps: S1, reacting 2-pyrrolidone and di-tert-butyl dicarbonate ester in an organic solvent by using 4-dimethylaminopyridine as a catalyst to obtain 1-(tert-butoxycarbonyl)-2-pyrrolidone; s2, dissolving the obtained 1-(tert-butoxycarbonyl)-2-pyrrolidone in a solvent, adding the solution into a 1, 3-propane diamine solution, carrying out stirring and reaction until the reaction is finished, and carrying out post-treatment to obtain [3-(3-amino-alanyl carbamoyl) propyl]-tert-butyl carbamate; s3, dissolving in a solvent, reducing by a reducing agent, and performing post-treatment to obtain [4-(3-amino-propylamino) butyl]-tert-butyl carbamate; and S4, dissolving in a solvent, dropwise adding hydrochloric acid for reaction to remove a protecting group, and after the reaction, further treating to obtain the spermidine. The raw materials such as pyrrolidone, 1, 3-propane diamine and the like are common chemical raw materials, the cost is relatively low, the reaction conditions are relatively mild, and the potential safety hazard in the reaction is relatively low.

Method for preparing spermidine

The invention belongs to the field of chemical synthesis and particularly relates to a method for preparing spermidine. The method comprises the steps that the spermidine is prepared through the mainprocess steps of reduction, amino protection and the like after reaction of amino-1-propanol and butyrolactone serving as raw materials. The method has the advantages of being simple in operation, high in product quality, high in yield and the like.