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BOC-N-Methyl-L-alanine is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

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  • 16948-16-6 Structure
  • Basic information

    1. Product Name: BOC-N-Methyl-L-alanine
    2. Synonyms: BOC-L-MEALA-OH;BOC-N-ALPHA-METHYL-L-ALANINE;BOC-MEALA-OH;BOC-N-ME-ALANINE;BOC-N-ME-ALA-OH;BOC-N-ME-S-ALA-OH;BOC-N-METHYL-L-ALANINE;BOC-N-METHYL-L-ALA-OH
    3. CAS NO:16948-16-6
    4. Molecular Formula: C9H17NO4
    5. Molecular Weight: 203.24
    6. EINECS: 1533716-785-6
    7. Product Categories: Alanine [Ala, A];N-Methyl Amino Acids;Boc-Amino acid series;Amino Acids & Derivatives;Chiral Reagents;amino acids;Pyrazoles
    8. Mol File: 16948-16-6.mol
  • Chemical Properties

    1. Melting Point: 88-92 °C
    2. Boiling Point: 296.3 °C at 760 mmHg
    3. Flash Point: 133 °C
    4. Appearance: /
    5. Density: 1.111 g/cm3
    6. Vapor Pressure: 0.00035mmHg at 25°C
    7. Refractive Index: 1.466
    8. Storage Temp.: Store at RT.
    9. Solubility: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
    10. PKA: 4.03±0.10(Predicted)
    11. BRN: 2366513
    12. CAS DataBase Reference: BOC-N-Methyl-L-alanine(CAS DataBase Reference)
    13. NIST Chemistry Reference: BOC-N-Methyl-L-alanine(16948-16-6)
    14. EPA Substance Registry System: BOC-N-Methyl-L-alanine(16948-16-6)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 16948-16-6(Hazardous Substances Data)

16948-16-6 Usage

Chemical Properties

White powder

Uses

Boc-N-methyl-L-alanine can be used in peptide synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 16948-16-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,9,4 and 8 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 16948-16:
(7*1)+(6*6)+(5*9)+(4*4)+(3*8)+(2*1)+(1*6)=136
136 % 10 = 6
So 16948-16-6 is a valid CAS Registry Number.
InChI:InChI=1/C9H17NO4/c1-6(7(11)12)10(5)8(13)14-9(2,3)4/h6H,1-5H3,(H,11,12)/t6-/m0/s1

16948-16-6 Well-known Company Product Price

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  • TCI America

  • (B3651)  N-(tert-Butoxycarbonyl)-N-methyl-L-alanine  >98.0%(GC)(T)

  • 16948-16-6

  • 5g

  • 830.00CNY

  • Detail
  • TCI America

  • (B3651)  N-(tert-Butoxycarbonyl)-N-methyl-L-alanine  >98.0%(GC)(T)

  • 16948-16-6

  • 25g

  • 2,750.00CNY

  • Detail
  • Alfa Aesar

  • (H31317)  N-Boc-N-methyl-L-alanine, 98%   

  • 16948-16-6

  • 1g

  • 1070.0CNY

  • Detail
  • Alfa Aesar

  • (H31317)  N-Boc-N-methyl-L-alanine, 98%   

  • 16948-16-6

  • 5g

  • 3566.0CNY

  • Detail
  • Aldrich

  • (15549)  Boc-N-Me-Ala-OH  ≥99.0% (TLC)

  • 16948-16-6

  • 15549-1G

  • CNY

  • Detail
  • Aldrich

  • (15549)  Boc-N-Me-Ala-OH  ≥99.0% (TLC)

  • 16948-16-6

  • 15549-5G

  • 2,727.27CNY

  • Detail

16948-16-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Boc-Nalpha-methyl-L-alanine

1.2 Other means of identification

Product number -
Other names N-(tert-Butoxycarbonyl)-N-Methyl-L-alanine

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:16948-16-6 SDS

16948-16-6Downstream Products

16948-16-6Relevant articles and documents

SUBSTITUTED 1,1'-BIPHENYL COMPOUNDS AND METHODS USING SAME

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Page/Page column 654-655, (2021/08/13)

The present invention includes substituted 1,1'-biphenyl compounds, analogues thereof, and compositions comprising the same. In one aspect, the compounds contemplated in the invention can be used to treat, ameliorate, or prevent hepatitis B virus (HBV) and/or hepatitis D virus (HDV) infections in a patient. In another aspect, the compounds contemplated in the invention can be used to treat, ameliorate, and/or prevent cancer in a patient.

Structure-Activity Relationship Study of Majusculamides A and B and Their Analogues on Osteogenic Activity

Nakajima, Daisuke,Natsume, Noriyuki,Ozaki, Kaori,Teruya, Toshiaki,Yokoshima, Satoshi

supporting information, p. 2477 - 2482 (2020/10/02)

We discovered that majusculamide A (1) and majusculamide B (2), isolated from a marine cyanobacterium collected in Okinawa, induced osteoblast differentiation in MC3T3-E1 cells. Although majusculamide A (1) has a different configuration only at the C-19 stereocenter, bearing a methyl group, compared to majusculamide B (2), the effect of 1 was stronger than that of 2. We synthesized some analogues of the majusculamides (3-15) and evaluated osteogenic activities of these analogues. The structure-activity relationship study of majusculamide analogues suggested that the number of methyls and configuration at C-19 and the nature of the substituent at C-20 of majusculamide A (1) may be important for the osteoblast differentiation-inducing effect of 1.

Tetrazole as a Replacement of the Electrophilic Group in Characteristic Prolyl Oligopeptidase Inhibitors

Kilpel?inen, Tommi P.,Tyni, Jonna K.,Lahtela-Kakkonen, Maija K.,Etel?inen, Tony S.,My?h?nen, Timo T.,Wallén, Erik A. A.

supporting information, p. 1635 - 1640 (2019/12/02)

4-Phenylbutanoyl-aminoacyl-2(S)-tetrazolylpyrrolidines were studied as prolyl oligopeptidase inhibitors. The compounds were more potent than expected from the assumption that the tetrazole would also here be a bioisostere of the carboxylic acid group and the corresponding carboxylic acids are at their best only weak inhibitors. The aminoacyl groups l-prolyl and l-alanyl gave potent inhibitors with IC50 values of 12 and 129 nM, respectively. This was in line with typical prolyl oligopeptidase inhibitors; however, we did observe a difference with N-methyl-l-alanyl, which gave potent inhibitors in typical prolyl oligopeptidase inhibitors but not in our novel compound series. Furthermore, all studied 4-phenylbutanoyl-aminoacyl-2(S)-tetrazolylpyrrolidines decreased α-synuclein dimerization at the concentration of 10 μM, also when they were only weak inhibitors of the proteolytic activity of the enzyme with an IC50 value of 205 μM. Molecular docking studies revealed that the compounds are likely to bind differently to the enzyme compared to typical prolyl oligopeptidase inhibitors represented in this study by 4-phenylbutanoyl-aminoacyl-2(S)-cyanopyrrolidines.

A novel route towards cycle-tail peptides using oxime resin: Teaching an old dog a new trick

Bérubé, Christopher,Borgia, Alexandre,Voyer, Normand

supporting information, p. 9117 - 9123 (2019/01/03)

Two anabaenopeptins, Schizopeptin 791 and anabaenopeptin NZ825, have similar structural features and have been synthesized via a novel acid-catalyzed head-to-side-chain concomitant cyclization/cleavage reaction on oxime resin. The methodology gave rapid access to the anabaenopeptin scaffold by taking advantage of a combined solid-phase/solution-phase synthetic strategy. Also, as side-products of the synthesis, large C2-symmetric 38-member cyclic peptides ring bearing two endocyclic lysine side-chains were isolated, constituting a novel cyclic peptide scaffold.

Preparation method of N-methylamino acid with optical configurations

-

Paragraph 0033; 0036; 0037, (2017/08/29)

The invention belongs to the field of medicine synthesis, relates to a preparation method of N-methylamino acid with optical configurations and in particular relates to a preparation method of N-methylamino acid with an R configuration and an S configuration. The preparation method is shown in the description. According to the preparation method provided by the invention, the configurations of reactants are transformed to obtain the N-methylamino acid with corresponding opposite configurations, and the preparation method is suitable for commercial scale production.

Phase I metabolites of mephedrone display biological activity as substrates at monoamine transporters

Mayer,Wimmer,Dillon-Carter,Partilla,Burchardt,Mihovilovic,Baumann,Sitte

supporting information, p. 2657 - 2668 (2016/10/19)

Background and Purpose: 4-Methyl-N-methylcathinone (mephedrone) is a synthetic stimulant that acts as a substrate-type releaser at transporters for dopamine (DAT), noradrenaline (NET) and 5-HT (SERT). Upon systemic administration, mephedrone is metabolized to several phase I compounds: the N-demethylated metabolite, 4-methylcathinone (nor-mephedrone); the ring-hydroxylated metabolite, 4-hydroxytolylmephedrone (4-OH-mephedrone); and the reduced keto-metabolite, dihydromephedrone. Experimental Approach: We used in vitro assays to compare the effects of mephedrone and synthetically prepared metabolites on transporter-mediated uptake and release in HEK293 cells expressing human monoamine transporters and in rat brain synaptosomes. In vivo microdialysis was employed to examine the effects of i.v. metabolite injection (1 and 3?mg·kg?1) on extracellular dopamine and 5-HT levels in rat nucleus accumbens. Key Results: In cells expressing transporters, mephedrone and its metabolites inhibited uptake, although dihydromephedrone was weak overall. In cells and synaptosomes, nor-mephedrone and 4-OH-mephedrone served as transportable substrates, inducing release via monoamine transporters. When administered to rats, mephedrone and nor-mephedrone produced elevations in extracellular dopamine and 5-HT, whereas 4-OH-mephedrone did not. Mephedrone and nor-mephedrone, but not 4-OH-mephedrone, induced locomotor activity. Conclusions and Implications: Our results demonstrate that phase I metabolites of mephedrone are transporter substrates (i.e. releasers) at DAT, NET and SERT, but dihydromephedrone is weak in this regard. When administered in vivo, nor-mephedrone increases extracellular dopamine and 5-HT in the brain whereas 4-OH-mephedrone does not, suggesting the latter metabolite does not penetrate the blood–brain barrier. Future studies should examine the pharmacokinetics of nor-mephedrone to determine its possible contribution to the in vivo effects produced by mephedrone.

Design, synthesis, and in vitro antiplasmodial activity of 4-aminoquinolines containing modified amino acid conjugates

Srinivasarao, Kondaparla,Agarwal, Pooja,Srivastava, Kumkum,Haq,Puri, Sunil K.,Katti

, p. 1148 - 1162 (2016/07/06)

Abstract: A new series of side chain-modified 4-aminoquinolines were synthesized and screened for in vitro antiplasmodial activity against both chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of Plasmodium falciparum. Among the series, compounds 30 and 31 showed significant inhibition of parasite growth against K1 strain of P. falciparum with IC50 values 0.28 and 0.31?μM, respectively, whereas compounds 34, 35, and 38 exhibited superior activity against K1 strain with IC50 values 0.18, 0.22, and 0.17?μM, respectively, as compared to 0.255?μM for chloroquine (CQ). All the compounds displayed good resistance factor between 1.54 and >34.48 as against 51.0 for CQ. All these analogues were found to form strong complex with hematin and inhibited the β-hematin formation in vitro, suggesting that this class of compounds act on a heme polymerization target. Overall results suggest that present series of compounds appear to be promising for further lead optimization to obtain compounds active against drug-resistant parasites. Graphical Abstract: [Figure not available: see fulltext.]

Total synthesis and absolute configuration of epicoccamide D, a naturally occurring mannosylated 3-acyltetramic acid

Loscher, Sebastian,Schobert, Rainer

supporting information, p. 10619 - 10624 (2013/08/23)

The endofungal metabolite epicoccamide D was synthesised in eighteen steps and 17 % yield as the first member of the family of natural glycotetramic acids. The modular character of the synthesis opens access also to analogues featuring different sugars and spacers. It comprises several high-yielding key steps. The β-D-mannosyl group was introduced by using an α-D-glucosyl imidate donor with subsequent oxidative-reductive epimerisation at C-2′. The pyrrolidine ring was closed quantitatively by a Lacey-Dieckmann condensation of an N-(β-ketoacyl)-N-methyl alaninate. The resulting 3-[ω-(β-D- mannosyl)octadec-2-enoyl]tetramic acid was hydrogenated in the presence of the rhodium catalyst (R,R)-[Rh(Et-DUPHOS)][BF4] to establish the (7S)-stereocentre. This was possible only after blocking the acyltetramic acid as a BF2-chelate to prevent capture of the metal catalyst. We also assigned the hitherto unknown configuration of the natural product as being 5S,7S by comparison of its 13C NMR spectroscopic and optical rotation data with those of our two synthetic 5S,7R/S-diasteromers. Copyright

Design, SAR, angiogenic activities evaluation and pro-angiogenic mechanism of new marine cyclopeptide analogs

Li,Lu,Wu,Yu,Xu,Qiu,Pei,Lin,Pang

, p. 1183 - 1194 (2013/07/28)

Angiogenesis plays an important role in a wide range of physiological processes. In this paper, we designed and synthesized a series of new analogs including 11 line-peptides and 9 cyclo-peptides by using a marine cyclopeptide (compound 21) which could st

Total synthesis, absolute configuration, and biological activity of xyloallenoide A

Wang, San-Yong,Xu, Zhong-Liang,Wang, Hui,Li, Chun-Rong,Fu, Li-Wu,Pang, Ji-Yan,Li, Jing,She, Zhi-Gang,Lin, Yong-Cheng

experimental part, p. 973 - 982 (2012/08/08)

The novel natural product xyloallenoide A, isolated from the marine mangrove endophytic fungus from the South China Sea, and its diastereoisomer xyloallenoide A1, which contain N-methyl-substituted amino acids, were synthesized. The absolute configurations of the amino acid units of xyloallenoide A were finally confirmed to be L-Lys, Me-D-Val, and Me-L-Ala. This report represents a practical and attractive alternative for the synthesis of N-methyl-substituted cyclotripeptides. In the preliminary bioassay, synthetic xyloallenoide A showed marginal activities against KB (IC50=9.6 mm) and KBv200 cells (IC50=10.3 μm), and xyloallenoide A1 was inactive against KB and KBv200 cells.

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