니코틴아마이드모노뉴클레오타이드

니코틴아마이드모노뉴클레오타이드
니코틴아마이드모노뉴클레오타이드 구조식 이미지
카스 번호:
1094-61-7
한글명:
니코틴아마이드모노뉴클레오타이드
동의어(한글):
니코틴아마이드모노뉴클레오타이드;베타-니코틴아미드모노뉴클레오티드
상품명:
β-Nicotinamide Mononucleotide
동의어(영문):
NMN;NICOTINAMIDE MONONUCLEOTIDE;NICOTINAMIDE RIBOTIDE;BETA-NICOTINAMIDE MONONUCLEOTIDE;BETA-NMN;β-NMN;B-NICOTINAMIDE MONONUCLEOTIDE;NMN powder;NicotinaMide Ribonucleotide;β-Nicotinamide Mononucleotide(NMN)
CBNumber:
CB6281591
분자식:
C11H15N2O8P
포뮬러 무게:
334.22
MOL 파일:
1094-61-7.mol
MSDS 파일:
SDS

니코틴아마이드모노뉴클레오타이드 속성

녹는점
166 °C(dec.)
저장 조건
-20°C
용해도
DMSO(약간 용해됨, 가열), 메탄올(약간 용해됨), 물(약간 용해됨)
물리적 상태
고체
물리적 상태
단단한 모양
색상
흰색에서 노란색으로
Merck
13,6697
BRN
3570187
안정성
흡습성이 매우 높음
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-/s3
InChIKey
DAYLJWODMCOQEW-TURQNECASA-N
SMILES
O[C@@H]1[C@@H]([C@@H](COP(O)([O-])=O)O[C@H]1[N+]1=CC=CC(C(=O)N)=C1)O |&1:1,2,3,11,r|
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
WGK 독일 3
F 고인화성물질 8-10-21
HS 번호 2934999090
그림문자(GHS): GHS hazard pictograms
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 GHS hazard pictograms P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고 GHS hazard pictograms
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.

니코틴아마이드모노뉴클레오타이드 C화학적 특성, 용도, 생산

용도

베타 - 니코틴 아미드 모노 뉴클레오타이드 그것은 인간의 세포 에너지 생산에 중요한 역할을합니다. 심혈관 질환, 뇌 혈관 질환, 호흡기 질환, 제 1 형 당뇨병 및 염증성 면역 질환의 치료에있어 약리학 적 효과의 측면으로는 세포 재생, 노화 방지 등과 같은 세포 에너지 전환에 중요한 코엔자임 니코틴 아미드 아데닌 디 뉴클레오티드의 합성에 참여합니다. 그것은 광범위한 적용 가능성을 가지고 있습니다.

개요

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+.

화학적 성질

White to Yellowish lyophilized powder

용도

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.

정의

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(-).

주요 응용

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.

제조 방법

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

benefits

As one of the primary precursors of NAD+ and intermediaries in NAD+ biosynthesis, NMN is as essential as NAD+ in the body’s proper functioning of cells.  NAD helps cells regulate a number of essential functions that help keep your cells running smoothly, including:energy metabolism, DNA repair, gene expression, and cellular stress responses.

일반 설명

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+.

Biochem/physiol Actions

In light of metabolic control mechanisms and many reports on β-Nicotinamide Mononucleotide (β-NMN), β-NMN is likely to be more effective as an NAD+ precursor than Nam. Research has compared the blood total NAD (NAD++NADH) and urinary excretion amounts of NAD+ catabolites in β-NMN- and Nam-administered rats. The concentration of blood total NAD and liver total NAD showed no significant differences among the three groups. However, when examining the kinetics of the urinary excretion, the urinary excretion of the SUM was lower in the β-NMN group than in the Nam group at 3-6 h after the administration. Moreover, the percentage of the urinary SUM was much lower in the β-NMN group than in the Nam group at 3-6 h. This result suggests that β-NMN is retained in the body for longer than Nam is. In addition, this result means that β-NMN has a higher turnover of salvage biosynthesis of NAD+ than Nam does. The resulting phenomenon accelerates the turnover of salvage biosynthesis of NAD+, which activates the SIRT1 reaction because SIRT1 (histone deacetylase) needs NAD+. Deacetylated histone molecules induce DNA silencing, contributing to anti-aging and longevity. When β-NMN is intraperitoneally injected, β-NMN is dephosphorylated in the blood to form Nam riboside (NR), which is then transported into the cells. NR is re-phosphorylated to form β-NMN, which is then synthesized to NAD+ in the nucleus. In contrast to Nam, which is controlled at the Nam→β-NMN reaction, the β-NMN biosynthesis pathway is not regulated[1]. 

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.]

니코틴아마이드모노뉴클레오타이드 준비 용품 및 원자재

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