Welcome to LookChem.com Sign In|Join Free

CAS

  • or

1094-61-7

Post Buying Request

1094-61-7 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

1094-61-7 Usage

Description

Nicotinamide mononucleotide (NMN), a product of the NAMPT reaction and a key NAD+ intermediate, ameliorates glucose intolerance by restoring NAD+ levels in HFD-induced T2D mice. NMN also enhances hepatic insulin sensitivity and restores gene expression related to oxidative stress, inflammatory response, and circadian rhythm, partly through SIRT1 activation. NMN is used for studying binding motifs within RNA aptamers and ribozyme activation processes involving β-nicotinamide mononucleotide (β-NMN)-activated RNA fragments.β-Nicotinamide mononucleotide (β-NMN) is an intermediate in the nicotinamide phosphoribosyltransferase (NAMPT)-catalyzed biosynthesis of nicotinamide adenine dinucleotide (NAD+). NAMPT mediates the condensation of nicotinamide with 5-phosphoribosyl-1-pyrophosphate to produce β-NMN. β-NMN adenyltransferase subsequently converts β-NMN to NAD+.

Chemical Properties

White to Yellowish lyophilized powder

Uses

β-Nicotinamide mononucleotide (NMN) is used to study binding motifs within RNA aptamers and ribozyme activation processes involving β-nicotinamide mononucleotide (β-NMN)-activated RNA fragments. NMN is a nucleotide derived from ribose and nicotinamide. Niacinamide (nicotinamide,) is a derivative of vitamin B3, also known as niacin.) As a biochemical precursor of NAD+, it may be useful in the prevention of pellagra.β-Nicotinamide mononucleotide is an intermediate in the biosynthesis of nicotinamide adenine dinucleotide (NAD+). Nicotinamide phosphoribosyltransferase (Nampt) catalyzes the condensation of nicotinamide with 5-phosphoribosyl-1-pyrophosphate to generate β-NMN, which is subsequently converted to NAD+ by β-NMN adenyltransferase.At 50-100 μM, β-NMN has been used to enhance NAD biosynthesis and glucose-stimulated insulin secretion in a Nampt+/- mouse model of metabolic disease, demonstrating a role for Nampt in β cell function.Furthermore, at 500 mg/kg/day, it has been shown to ameliorate glucose intolerance in high-fat diet-induced type 2 diabetes mice by restoring NAD+ levels.

Preparation

β-Nicotinamide mononucleotide is a NAD+intermediate. In recent years, the relation of NAD+metabolism and aging-associated disease is attracting attention from various research fields. Synthesis of β-nicotinamide mononucleotide (NMN) A solution of NAD (3.5 g, 5.28 mmol) and ZrCl4(6.15 g, 26.4 mmol) in 500 ml water was stirred at 50°C for 30 min. The hydrolysis was monitored by TLC (SiO2EtOH/ 1 M NH4Ac [7 : 3]). The reaction was quenched with 245mL of a 0.5 M solution of Na3PO4. After adjusting to pH 7 with a 2 M solution of HCl, a white precipitate was formed. The suspension was centrifuged 8 min,1,000rpm, the supernatant was collected and the pellet was washed two times with 200 mL water. The combined supernatants wereconcentrated to 1/3 of its volume on a rotary evaporator. The remaining solution was purified with a column filled with Dowex 50WX8 (100-200 mesh, H+-Form, column-material: 2.5 x 30 cm). The column was loaded with 1.5 L5 % HCl and equilibrated with1.5L millipore water until pH 5 was reached. 100 mL of the concentrated solution was loaded on the ion exchange column and eluted with Milliporewater. The first cleavage product eluted was NMN (615 mg, 1.84 mmol,yield:35 %) and yielded a colorless solid after evaporation of the solvent, followed by AMP. 1H NMR (500MHz, D2O)δ: 9.48 (s, 1 H), 9.31 (d,J= 6.2 Hz, 1 H), 9.00 (d,J= 8.2 Hz, 1 H), 8.32 (dd,J= 8.2, 6.2 Hz, 1 H), 6.24 (d,J=5.4 Hz, 1 H), 4.68-4.64 (m, 1 H), 4.58 (t, 1 H), 4.48-4.45 (m, 1 H), 4.36–4.14 (m,J= 12.0, 2 H). 13C NMR (75 MHz, d2o) δ: 165.50, 145.65, 142.15, 139.53, 133.62, 128.19, 99.65, 87.18, 87.06, 77.42, 70.71, 63.89, 63.82. 31P NMR (202 MHz, D2O)δ:-0.03

Definition

ChEBI: β-Nicotinamide Mononucleotide is a condensation product of nicotinamide and ribose 5-phosphate, in which the nitrogen of nicotinamide is linked to the (β) c-l of the ribose. NMN zwitterion is a nicotinamide mononucleotide. It has a role as an Escherichia coli metabolite and a mouse metabolite. It is a conjugate base of a NMN(+). It is a conjugate acid of a NMN(-).

Application

β-Nicotinamide mononucleotide (NMN) is a product of the extracellular Nicotinamide phosphoribosyltransferase (eNAMPT) reaction and a key NAD+ intermediate. It ameliorates glucose intolerance by restoring NAD+ levels in HFD-induced T2D mice . It also enhances hepatic insulin sensitivity and restores gene expression related to oxidative stress, inflammatory response, and circadian rhythm, partly through SIRT1 activation. It is used to study binding motifs within RNA aptamers and ribozyme activation processes involving β-nicotinamide mononucleotide (β-NMN)-activated RNA fragments.

General Description

β-Nicotinamide mononucleotide (β-NMN) is an intermediate in the nicotinamide phosphoribosyltransferase (NAMPT)-catalyzed biosynthesis of nicotinamide adenine dinucleotide (NAD+). NAMPT mediates the condensation of nicotinamide with 5-phosphoribosyl-1-pyrophosphate to produce β-NMN. β-NMN adenyltransferase subsequently converts β-NMN to NAD+.

in vitro

β-nicotinamide mononucleotide has several beneficial pharmacological activities. Mostly mediated by its involvement in NAD+ biosynthesis, the pharmacological activities of NMN include its role in cellular biochemical functions, cardioprotection, diabetes, Alzheimer's disease, and complications associated with obesity.The intracellular NAD+ levels are significantly decreased by knockdown or knockout of Nampt (Nampt KD or Nampt KO) or treatment with Nampt inhibitor FK866, whereas NAD+ levels are dramatically increased by supplement of NAD+ precursors NAM or NMN (0.5–1 mM). NAD+ precursor NMN treatment inhibited CD8+ T cells activation and function.

in vivo

β-Nicotinamide mononucleotide (500 mg/kg; i.p.; 3 times per week for 7-10 week) prevents mtDNA damage and Dox-induced cardiac dysfunction.Nampt KO markedly inhibits tumor progression, whereas Nampt metabolite β-Nicotinamide mononucleotide (300 mg/kg body weight; i.p.; once every two days for 2 weeks) significantly promotes tumor growth in C57BL/6 mice (bearing wildtype Hepa1-6 cells). The reduction and increase in NAD+ level of respective Nampt KO and β-Nicotinamide mononucleotide-treated tumors are confirmed.β-nicotinamide mononucleotide ameliorates glucose intolerance by restoring NAD(+) levels in HFD-induced T2D mice. β-nicotinamide mononucleotide also enhances hepatic insulin sensitivity and restores gene expression related to oxidative stress, inflammatory response, and circadian rhythm, partly through SIRT1 activation.

Purification Methods

Purify NMN by passage through a column of Dowex-1 (Clform) and washing with H2O until no absorbance is observed at 260 nm. The tubes containing NMN are pooled, adjusted to pH 5.5-6 and evaporated in vacuo to a small volume. This is adjusted to pH 3 with dilute HNO3 in an ice-bath and treated with 20volumes of Me2CO at 0-5o. The heavy white precipitate is collected by centrifugation at 0o. It is best stored wet and frozen or it can be dried to give a gummy residue. It has max 266nm ( 4,600) and min 249nm ( 3600) at pH 7.0 (i.e. no absorption at 340nm). It can be estimated by reaction with CNor hydrosulfite which form the 4-adducts (equivalent to NADH) which have UV max 340nm ( 6,200). Thus after reaction, an OD340 of one is obtained from a 0.1612mM solution in a 1cm path cuvette. [Plaut & Plaut Biochemical Preparations 5 56 1957, Maplan & Stolzenbach Methods Enzymol 3 899 1957, Kaplan et al. J Am Chem Soc 77 815 1955, Beilstein 22/2 V 168.]

Check Digit Verification of cas no

The CAS Registry Mumber 1094-61-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,9 and 4 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1094-61:
(6*1)+(5*0)+(4*9)+(3*4)+(2*6)+(1*1)=67
67 % 10 = 7
So 1094-61-7 is a valid CAS Registry Number.
InChI:InChI=1/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/t7-,8-,9-,11-/m1/s1

1094-61-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name NMN zwitterion

1.2 Other means of identification

Product number -
Other names Beta-Nicotinamide Mononucleotide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1094-61-7 SDS

1094-61-7Synthetic route

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
With trimethyl phosphite; trichlorophosphate at 0℃; for 12h; Inert atmosphere;88.27%
Stage #1: 3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside) With Sodium trimetaphosphate; sodium hydroxide In water at 30℃; for 4h; pH=9;
Stage #2: With hydrogenchloride In water at 10℃; Reagent/catalyst;
68%
With nitromethane; water; trichlorophosphate
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium bromide
78687-39-5

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium bromide

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
With trimethyl phosphite; trichlorophosphate at -5 - 0℃; for 7h;80%
With trimethyl phosphite; trichlorophosphate at 0℃; for 4h;64%
(3,4-dihydroxy-5-(3-(ethoxycarbonyl)pyridin-1-ium-1-yl)tetrahydrofuran-2-yl)methyl hydrogen phosphate

(3,4-dihydroxy-5-(3-(ethoxycarbonyl)pyridin-1-ium-1-yl)tetrahydrofuran-2-yl)methyl hydrogen phosphate

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
With ammonia In acetonitrile at -5 - 5℃; for 1h;80%
nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; ammonium acetate; zirconium(IV) chloride In ethanol at 50℃; for 0.5h; pH 5;70%
With water; zirconium(IV) chloride at 80℃; for 0.5h; Reagent/catalyst;
C23H24N2O8P(1+)*Cl(1-)

C23H24N2O8P(1+)*Cl(1-)

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
With platinum(IV) oxide; hydrogen In deuteromethanol for 12h; Reagent/catalyst;64%
1-(β-D-ribofuranosyl)-nicotinamide
1341-23-7

1-(β-D-ribofuranosyl)-nicotinamide

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
With trichlorophosphate In tetrahydrofuran at 0 - 20℃; for 12h;56%
3-carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride
53406-00-1

3-carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride

ribose 5-phosphate bis(cyclohexylammonium) salt
87763-86-8

ribose 5-phosphate bis(cyclohexylammonium) salt

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
With ammonia 1.) -60 deg C, 36 h; r.t., 1 h; 2.) methanol, ethylene glycol (1:1), 4 deg C, 11 h;35%
nicotinamide
98-92-0

nicotinamide

5-phosphoribosyl-1-pyrophosphate
97-55-2, 7540-64-9, 99945-37-6, 130384-52-0

5-phosphoribosyl-1-pyrophosphate

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Enzym aus Erythrocyten;
3-carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride
53406-00-1

3-carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride

phosphoribosylamine
14050-66-9

phosphoribosylamine

A

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

B

α-nicotinamide mononucleotide
7298-94-4

α-nicotinamide mononucleotide

C

2,4-Dinitroanilin
97-02-9

2,4-Dinitroanilin

Conditions
ConditionsYield
In methanol at 5℃; for 14h; Yield given;
In methanol at 5℃; for 14h;
β-NAD

β-NAD

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
enzymatische Spaltung;
N1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-3-aminocarbonylpyridinium bromide
18784-01-5

N1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-3-aminocarbonylpyridinium bromide

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH3 / methanol
2: 80 percent / POCl3, PO(OMe)3 / 7 h / -5 - 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 55 percent / NH3 / methanol / 72 h / -18 °C
2: 64 percent / Phosphoryl chloride, trimethyl phosphate / 4 h / 0 °C
View Scheme
N1-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-3-aminocarbonylpyridinium bromide
78687-38-4

N1-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-3-aminocarbonylpyridinium bromide

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / NH3 / methanol / 20 h / -5 - -3 °C
2: 80 percent / POCl3, PO(OMe)3 / 7 h / -5 - 0 °C
View Scheme
adenosine 5'-monophosphate
47287-36-5, 119923-66-9

adenosine 5'-monophosphate

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / 1.) H(+), H2O / 1.) 100 deg C, 6 min; 2.) 0 deg C
2: 35 percent / NH3 / 1.) -60 deg C, 36 h; r.t., 1 h; 2.) methanol, ethylene glycol (1:1), 4 deg C, 11 h
View Scheme
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose
6974-32-9

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: HBr / CH2Cl2 / 3 h / -20 °C
2: liquid sulphur dioxide
3: 55 percent / NH3 / methanol / 72 h / -18 °C
4: 64 percent / Phosphoryl chloride, trimethyl phosphate / 4 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogen chloride; diethyl ether
2: acetonitrile
3: NH3; methanol
4: POCl3; nitromethane; H2O
View Scheme
2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide
22860-91-9

2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: liquid sulphur dioxide
2: 55 percent / NH3 / methanol / 72 h / -18 °C
3: 64 percent / Phosphoryl chloride, trimethyl phosphate / 4 h / 0 °C
View Scheme
2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride
105499-44-3

2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetonitrile
2: NH3; methanol
3: POCl3; nitromethane; H2O
View Scheme
nicotinamide
98-92-0

nicotinamide

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetonitrile
2: NH3; methanol
3: POCl3; nitromethane; H2O
View Scheme
Multi-step reaction with 3 steps
1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C
2: sodium ethanolate / ethanol / 1 h / -5 - 5 °C
3: trichlorophosphate / tetrahydrofuran / 12 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: ammonium sulfate / 8 h / 125 °C
2.1: tin(IV) chloride / dichloromethane / 1.5 h / 55 °C
2.2: 0.75 h / 0 °C
3.1: methanol; propylamine / 22 h / -5 °C
4.1: trimethyl phosphite; trichlorophosphate / 12 h / 0 °C / Inert atmosphere
View Scheme
5’,3‘,2’-tri-O-acetyl-1-β-D-ribofuranosylnicotinamide chloride
109527-15-3

5’,3‘,2’-tri-O-acetyl-1-β-D-ribofuranosylnicotinamide chloride

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH3; methanol
2: POCl3; nitromethane; H2O
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / methanol / 12 h / Sealed tube
2: trichlorophosphate
View Scheme
3-carbamoyl-1-(tri-O-benzoyl-β-D-ribofuranosyl)-pyridinium; chloride
122620-02-4

3-carbamoyl-1-(tri-O-benzoyl-β-D-ribofuranosyl)-pyridinium; chloride

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH3; methanol
2: POCl3; nitromethane; H2O
View Scheme
2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride
5991-01-5

2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetonitrile
2: NH3; methanol
3: POCl3; nitromethane; H2O
View Scheme
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
With trimethyl phosphite; trichlorophosphate at -5 - 0℃; for 12h; Inert atmosphere;
pentasodium 5-phosphoribosyl 1-pyrophosphate

pentasodium 5-phosphoribosyl 1-pyrophosphate

nicotinamide
98-92-0

nicotinamide

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
With nicotinamide phosphoribosyltransferase; tris hydrochloride; ATP; magnesium chloride; D,L-dithiothreitol; bovine serum albumin In water at 37℃; Kinetics; Enzymatic reaction;

A

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

B

adenosine 5'-diphosphate
58-64-0

adenosine 5'-diphosphate

C

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With water; zirconium(IV) oxide at 80℃; for 48h;
[(2R,3R,4R)-3,4-diacetoxy-5-chlorotetrahydrofuran-2-yl]methyl acetate
40554-98-1

[(2R,3R,4R)-3,4-diacetoxy-5-chlorotetrahydrofuran-2-yl]methyl acetate

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetonitrile / 0.33 h / 70 °C
2: hydrogenchloride / methanol / 12 h / Sealed tube
3: trichlorophosphate
View Scheme
Multi-step reaction with 3 steps
1: acetonitrile / 50 °C
2: hydrogenchloride / methanol / 12 h / Sealed tube
3: trichlorophosphate
View Scheme
3-carbamoyl-1-((2R,3R,4R,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate

3-carbamoyl-1-((2R,3R,4R,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonia / methanol / 24 h / -9 - -8 °C
2: hydrogenchloride / methanol / 8 h / -8 - 0 °C
3: trimethyl phosphite; trichlorophosphate / 24 h / -10 - -7 °C
View Scheme
nicotinamide adenine dinucleotide
76961-04-1

nicotinamide adenine dinucleotide

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
With zirconium(IV) chloride In water at 50℃; for 1h;
nicotinamide
98-92-0

nicotinamide

5-phospho-α-D-ribosyl 1-pyrophosphate

5-phospho-α-D-ribosyl 1-pyrophosphate

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
With tris(3-hydroxypropyl)phosphine; nicotinamide phosphoribosyltransferase; tris hydrochloride; ATP; magnesium chloride In water at 37℃; pH=7.5; Kinetics; Reagent/catalyst; Enzymatic reaction;
1,2,3,5-tetraacetylribose
13035-61-5

1,2,3,5-tetraacetylribose

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C
2.1: ammonia / 1 h / -5 - 5 °C
2.2: 1 h / -5 - 5 °C
3.1: trichlorophosphate / tetrahydrofuran / 12 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C
2: sodium ethanolate / ethanol / 1 h / -5 - 5 °C
3: trichlorophosphate / tetrahydrofuran / 12 h / 0 - 20 °C
View Scheme
3-pyridinecarboxylic acid ethyl ester
614-18-6

3-pyridinecarboxylic acid ethyl ester

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C
2.1: ammonia / 1 h / -5 - 5 °C
2.2: 1 h / -5 - 5 °C
3.1: trichlorophosphate / tetrahydrofuran / 12 h / 0 - 20 °C
View Scheme
L-valine
72-18-4

L-valine

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

(S)-1-carboxy-2-methypropan-1-aminium ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

(S)-1-carboxy-2-methypropan-1-aminium ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In water at 10℃; pH=Ca. 3.8 - 4;100%
nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

L-histidine
71-00-1

L-histidine

(S)-1-carboxy-2-(1H-imidazol-4-yl)ethanaminium ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

(S)-1-carboxy-2-(1H-imidazol-4-yl)ethanaminium ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In water at 10℃; pH=Ca. 6 - 6.2;100%
L-threonine
72-19-5

L-threonine

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

(1S,2R)-1-carboxy-2-hydropropan-1-aminium ((2R,3R,4S,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

(1S,2R)-1-carboxy-2-hydropropan-1-aminium ((2R,3R,4S,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In water at 10℃; pH=Ca. 3.9 - 4.4;100%
nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

L-proline
147-85-3

L-proline

(S)-2-carboxypyrrolidin-1-ium ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

(S)-2-carboxypyrrolidin-1-ium ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In water at 10℃; pH=Ca. 3.3 - 3.9;100%
L-lysine
56-87-1

L-lysine

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

(S)-5-amino-5-carboxypentan-1-aminium ((2R,3R,4S,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

(S)-5-amino-5-carboxypentan-1-aminium ((2R,3R,4S,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In water at 10℃; pH=Ca. 6 - 6.2;100%
L-Aspartic acid
56-84-8

L-Aspartic acid

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

(S)-1,2-dicarboxyethan-1-aminium-((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

(S)-1,2-dicarboxyethan-1-aminium-((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In water pH=2.99 - 3.39; Inert atmosphere; Cooling with ice;100%
betaine
107-43-7

betaine

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

1-carboxy-N,N,N-trimethylmethanaminium ((2R,35,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

1-carboxy-N,N,N-trimethylmethanaminium ((2R,35,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In water at 10℃; for 0.166667h;97%
L-phenylalanine
63-91-2

L-phenylalanine

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

(S)-1-carboxy-2-phenylethan-1-aminium-((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

(S)-1-carboxy-2-phenylethan-1-aminium-((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In water pH=3.43 - 4; Cooling with ice;96%
L-Cysteine
52-90-4

L-Cysteine

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

(R)-1-carboxy-2-mercaptoethan-1-aminium-((2R,3R,4S,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

(R)-1-carboxy-2-mercaptoethan-1-aminium-((2R,3R,4S,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In water pH=3.38 - 3.86; Cooling with ice;95%
L-asparagine
70-47-3

L-asparagine

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

(S)-3-amino-1-carboxy-3-oxopropan-1-aminium-((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

(S)-3-amino-1-carboxy-3-oxopropan-1-aminium-((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In water pH=3.38 - 3.86; Cooling with ice;95%
nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

adenosine 5'-monophosphate
47287-36-5, 119923-66-9

adenosine 5'-monophosphate

nicotinamide adenine dinucleotide
76961-04-1

nicotinamide adenine dinucleotide

Conditions
ConditionsYield
With 1,3-dimercaptopropanol; AdK on PAN gel; NAD pyrophosphorylase; PPiase; potassium acetate; magnesium chloride In water for 3h; Ambient temperature; pH: 7.0;91%
L-methionine
63-68-3

L-methionine

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

(S)-1-carboxy-3-(methylthio)propan-1-aminium ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

(S)-1-carboxy-3-(methylthio)propan-1-aminium ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In water at 10℃; pH=Ca. 4.4 - 4.6;89%
morpholin-4-yl-phosphonic acid mono-5′-[6-(pyrrol-2-yl)-9-β-D-ribofuranosyl-purine]

morpholin-4-yl-phosphonic acid mono-5′-[6-(pyrrol-2-yl)-9-β-D-ribofuranosyl-purine]

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

P1-[6-(pyrrol-2-yl)-purine-9-β-D-ribofuranos-5'-yl]-P2-[nicotinamide-1-β-D-ribofuranos-5′-yl]pyrophosphate

P1-[6-(pyrrol-2-yl)-purine-9-β-D-ribofuranos-5'-yl]-P2-[nicotinamide-1-β-D-ribofuranos-5′-yl]pyrophosphate

Conditions
ConditionsYield
With magnesium sulfate; manganese(ll) chloride In formamide at 20℃; for 12h; Inert atmosphere;87%
nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

glycine
56-40-6

glycine

carboxymethanaminium ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methvl phosphate

carboxymethanaminium ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methvl phosphate

Conditions
ConditionsYield
In water pH=3.22 - 3.9; Inert atmosphere; Cooling with ice;85%
L-serin
56-45-1

L-serin

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

(S)-1-carboxy-2-hydroxyethan-1-aminium ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

(S)-1-carboxy-2-hydroxyethan-1-aminium ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In water pH=3.22 - 3.8; Inert atmosphere; Cooling with ice;83%
((2R,3R,4R,5R)-5-(4-aminothieno[3,4-d]pyrimidin-7-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen triphosphate

((2R,3R,4R,5R)-5-(4-aminothieno[3,4-d]pyrimidin-7-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen triphosphate

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

1-((2R,3R,4R,5R)-5-((((((((2R,3R,4R,5R)-5-(4-aminothieno[3,4-d]pyrimidin-7-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)methyl)- 3,4-dihydroxytetrahydrofuran-2-yl)-3-carbamoylpyridin-1-ium

1-((2R,3R,4R,5R)-5-((((((((2R,3R,4R,5R)-5-(4-aminothieno[3,4-d]pyrimidin-7-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)methyl)- 3,4-dihydroxytetrahydrofuran-2-yl)-3-carbamoylpyridin-1-ium

Conditions
ConditionsYield
With Saccharomyces cerevisiae inorganic pyrophosphatase; Homo sapiens recombinant nicotinamide mononucleotide adenylyl transferase 1; potassium chloride; sodium chloride; magnesium chloride In ethanol at 37℃; for 2.16667h; Enzymatic reaction;81%
7-deaza-8-bromoadenosine 5'-monophosphate morpholidate triethylammonium salt

7-deaza-8-bromoadenosine 5'-monophosphate morpholidate triethylammonium salt

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

7-deaza-8-bromo nicotinamide adenine dinucleotide triethylammonium salt
213894-71-4

7-deaza-8-bromo nicotinamide adenine dinucleotide triethylammonium salt

Conditions
ConditionsYield
With magnesium sulfate; formamide; manganese(ll) chloride at 20℃; for 48h;79%
L-alanin
56-41-7

L-alanin

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

C11H15N2O8P*C3H7NO2

C11H15N2O8P*C3H7NO2

Conditions
ConditionsYield
In water pH=3.22-3.8; Inert atmosphere; Cooling with ice;79%
C14H23N6O10P
1278592-46-3

C14H23N6O10P

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

C25H36N8O17P2
1278592-45-2

C25H36N8O17P2

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; magnesium chloride; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃;67%
nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

L-carnitine
541-15-1

L-carnitine

(R)-3-carboxy-2-hydroxy-N,N,N-trimethylpropan-1-aminium ((2R,35,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

(R)-3-carboxy-2-hydroxy-N,N,N-trimethylpropan-1-aminium ((2R,35,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In water at 10℃; for 0.166667h;67%
nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

acetic anhydride
108-24-7

acetic anhydride

2',3'-di-O-acetylnicotinamide mononucleotide
154591-45-4

2',3'-di-O-acetylnicotinamide mononucleotide

Conditions
ConditionsYield
With pyridine In water at 0℃; for 3h;65%
With pyridine In water at 0℃; for 48h;
With pyridine at 0 - 5℃; for 24h; Inert atmosphere;
With pyridine In water at -5 - 0℃; for 24h; Inert atmosphere;
6-N-methyladnenosine 5'-monophosphate morpholidated triethylammonium salt

6-N-methyladnenosine 5'-monophosphate morpholidated triethylammonium salt

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

6-N-methyl nicotinamide adenine dinucleotide triethylammonium salt

6-N-methyl nicotinamide adenine dinucleotide triethylammonium salt

Conditions
ConditionsYield
Stage #1: 6-N-methyladnenosine 5'-monophosphate morpholidated triethylammonium salt; nicotinamide mononucleotide With magnesium sulfate; manganese(ll) chloride In formamide at 20℃; for 48h; Inert atmosphere;
Stage #2: With triethylamine carbonate In formamide; acetonitrile
64%
C26H36N7O9P
1352621-63-6

C26H36N7O9P

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

8-(3-(Boc-aminomethyl)phenyl) NAD
1352621-54-5

8-(3-(Boc-aminomethyl)phenyl) NAD

Conditions
ConditionsYield
With magnesium sulfate; manganese(ll) chloride In formamide at 20℃; for 24h; Inert atmosphere;61%

1094-61-7Relevant articles and documents

Plaut,Plaut

, (1957)

A novel preparation of nicotinamide mononucleotide

Liu,Visscher

, p. 1215 - 1216 (1994)

Nicotinamide mononucleotide is conveniently prepared from nicotinamide adenine dinucleotide by specific hydrolysis of the pyrophosphate bond using the Zr4+ ion as catalyst.

Nicotinamide-Containing Di- and Trinucleotides as Chemical Tools for Studies of NAD-Capped RNAs

Mlynarska-Cieslak, Agnieszka,Depaix, Anais,Grudzien-Nogalska, Ewa,Sikorski, Pawel J.,Warminski, Marcin,Kiledjian, Megerditch,Jemielity, Jacek,Kowalska, Joanna

, p. 7650 - 7655 (2018)

We report the chemical synthesis of a set of nicotinamide adenine dinucleotide (NAD) cap analogues containing chemical modifications that reduce their susceptibility to NAD-RNA-degrading enzymes. These analogues can be incorporated into transcripts in a similar way as NAD. Biochemical characterization of RNAs carrying these caps with DXO, NudC, and Nudt12 enzymes led to the identification of compounds that can be instrumental in unraveling so far unaddressed biological aspects of NAD-RNAs.

Enzymatic and chemical syntheses of vacor analogs of nicotinamide riboside, nmn and nad

Sverkeli, Lars Jansen,Hayat, Faisal,Migaud, Marie E.,Ziegler, Mathias

, (2021)

It has recently been demonstrated that the rat poison vacor interferes with mammalian NAD metabolism, because it acts as a nicotinamide analog and is converted by enzymes of the NAD salvage pathway. Thereby, vacor is transformed into the NAD analog vacor adenine dinucleotide (VAD), a molecule that causes cell toxicity. Therefore, vacor may potentially be exploited to kill cancer cells. In this study, we have developed efficient enzymatic and chemical procedures to produce vacor analogs of NAD and nicotinamide riboside (NR). VAD was readily generated by a base-exchange reaction, replacing the nicotinamide moiety of NAD by vacor, catalyzed by Aplysia californica ADP ribosyl cyclase. Additionally, we present the chemical synthesis of the nucleoside version of vacor, vacor riboside (VR). Similar to the physiological NAD precursor, NR, VR was converted to the corresponding mononucleotide (VMN) by nicotinamide riboside kinases (NRKs). This conversion is quantitative and very efficient. Consequently, phosphorylation of VR by NRKs represents a valuable alternative to produce the vacor analog of NMN, compared to its generation from vacor by nicotinamide phosphoribosyltransferase (NamPT).

PRODUCTION OF NMN AND ITS DERIVATIVES VIA MICROBIAL PROCESSES

-

Paragraph 0028-0029; 0032-0036; 0070-0074; 0083, (2021/11/13)

The present invention relates to microbial production of nicotinamide mononucleotide (NMN), nicotinamide riboside (NR), and nicotinamide adenine dinucleotide (NAD) using a genetically modified bacterium.

Preparation method of beta-nicotinamide mononucleotide

-

, (2021/05/01)

The invention discloses a preparation method of beta-nicotinamide mononucleotide. According to the method disclosed by the invention, the beta-nicotinamide mononucleotide is prepared by taking a compound shown as a formula II as a raw material and sequentially carrying out glycosylation condensation, deprotection, phosphorylation and acylation protection group removal reaction. Compared with methods in the prior art, the method provided by the invention has the advantages of high yield, simple operation, easy purification of intermediates, good phosphorylation selectivity and the like.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 1094-61-7