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BOC-SER(TOS)-OCH3, also known as Boc-Ser(Tos)-OMe, is a chemical compound that serves as a protectant molecule in the synthesis of peptides. It is a derivative of serine, an amino acid, and is equipped with protective groups to prevent unwanted side reactions during peptide synthesis. The BOC (tert-butyloxycarbonyl) group shields the amine group, while the TOS (tosylate) group protects the hydroxyl side chain. The OCH3 (methoxy) group indicates methylation, which reduces the compound's reactivity and facilitates peptide coupling.

56926-94-4

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  • N-[(1,1-Dimethylethoxy)-carbonyl]-L-serine methyl ester 4-methylbenzenesulfonate ester

    Cas No: 56926-94-4

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  • L-Serine,N-[(1,1-dimethylethoxy)carbonyl]-O-[(4-methylphenyl)sulfonyl]-, methyl ester

    Cas No: 56926-94-4

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56926-94-4 Usage

Uses

Used in Pharmaceutical Industry:
BOC-SER(TOS)-OCH3 is used as a protected amino acid for the synthesis of peptides, which are essential components in the development of various pharmaceutical products. Its protective groups ensure that the serine amino acid remains stable and unreactive during the synthesis process, allowing for the creation of complex peptide structures with minimal side reactions.
Used in Biochemical Research:
In the field of biochemical research, BOC-SER(TOS)-OCH3 is used as a building block for the assembly of peptides and proteins. Its protective groups enable researchers to study the properties and functions of these biomolecules in a controlled manner, without the interference of unwanted side reactions.
Used in Peptide Synthesis:
BOC-SER(TOS)-OCH3 is used as a key component in the synthesis of peptides, which are short chains of amino acids linked by peptide bonds. The protective groups on BOC-SER(TOS)-OCH3 allow for the stepwise construction of peptide chains, with each amino acid being added in a controlled and precise manner. This is crucial for the production of peptides with specific sequences and functions.

Check Digit Verification of cas no

The CAS Registry Mumber 56926-94-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,6,9,2 and 6 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 56926-94:
(7*5)+(6*6)+(5*9)+(4*2)+(3*6)+(2*9)+(1*4)=164
164 % 10 = 4
So 56926-94-4 is a valid CAS Registry Number.
InChI:InChI=1/C16H23NO7S/c1-11-6-8-12(9-7-11)25(20,21)23-10-13(14(18)22-5)17-15(19)24-16(2,3)4/h6-9,13H,10H2,1-5H3,(H,17,19)/t13-/m0/s1

56926-94-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name Boc-Ser(Tos)-OMe

1.2 Other means of identification

Product number -
Other names methyl (2S)-3-(4-methylphenyl)sulfonyloxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

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:56926-94-4 SDS

56926-94-4Relevant articles and documents

Biosynthesis of the antibiotic tropodithietic acid by the marine bacterium Phaeobacter inhibens

Brock, Nelson L.,Nikolay, Alexander,Dickschat, Jeroen S.

, p. 5487 - 5489 (2014)

The biosynthesis of tropodithietic acid was investigated using a combinatorial approach of feeding experiments, gene knockouts and bioinformatic analyses. The mechanism of sulfur introduction is distinct from known mechanisms in holomycin, thiomarinol A a

Thioamycolamides A-E, Sulfur-Containing Cycliclipopeptides Produced by the Rare Actinomycete Amycolatopsis sp.

Pan, Chengqian,Kuranaga, Takefumi,Liu, Chao,Lu, Shan,Shinzato, Naoya,Kakeya, Hideaki

, p. 3014 - 3017 (2020)

A series of novel sulfur-containing cycliclipopeptides named thioamycolamides A-E, with thiazoline, thioether rings, and fatty acid moieties, were identified from the culture broth of the rare actinomycete Amycolatopsis sp. 26-4. The planar structural elu

Synthesis and Biological Evaluation of CF3Se-Substituted α-Amino Acid Derivatives

Han, Zhou-Zhou,Dong, Tao,Ming, Xiao-Xia,Kuang, Fu,Zhang, Cheng-Pan

supporting information, p. 3177 - 3180 (2021/07/28)

Several CF3Se-substituted α-amino acid derivatives, such as (R)-2-amino-3-((trifluoromethyl)selanyl)propanoates (5 a/6 a), (S)-2-amino-4-((trifluoromethyl)selanyl)butanoates (5 b/6 b), (2R,3R)-2-amino-3-((trifluoromethyl)selanyl)butanoates (5 c/6 c), (R)-2-((S)-2-amino-3-phenylpropanamido)-3-((trifluoromethyl)selanyl)propanoates (11 a/12 a), and (R)-2-(2-aminoacetamido)-3-((trifluoromethyl)selanyl)propanoates (11 b/12 b), were readily synthesized from natural amino acids and [Me4N][SeCF3]. The primary in vitro cytotoxicity assays revealed that compounds 6 a, 11 a and 12 a were more effective cell growth inhibitors than the other tested CF3Se-substituted derivatives towards MCF-7, HCT116, and SK-OV-3 cells, with their IC50 values being less than 10 μM for MCF-7 and HCT116 cells. This study indicated the potentials of CF3Se moiety as a pharmaceutically relevant group in the design and synthesis of novel biologically active molecules.

Synthesis, Fungicidal Activity, and Mechanism of Action of Pyrazole Amide and Ester Derivatives Based on Natural Products l -Serine and Waltherione Alkaloids

Chen, Yan,Cui, Yanhong,Gu, Yucheng,Guo, Shangjing,Hua, Xuewen,Liu, Wenrui,Liu, Xinghai,Liu, Yi,Ru, Jing,Sui, Junkang,Wang, Guiqing,Xue, Chenmeng,Yu, Xiaobo

, p. 11470 - 11484 (2021/10/12)

The development of new green fungicides based on the structural optimization of natural products can effectively solve the problems of low safety and high pathogen resistance of traditional fungicides. In this paper, based on pyrazole amide compound h-I-9 with excellent fungicidal activity discovered in the previous work, a series of l-serine-derived pyrazole amide and waltherione alkaloid-derived pyrazole ester derivatives were synthesized. The structures were successively identified by 1H NMR, 13C NMR, high-resolution mass spectrometry, and X-ray single-crystal diffraction. The in vitro and in vivo fungicidal activity screening demonstrated that compound II-5 showed a good inhibition rate against Physalospora piricola. A transmission electron microscope and fluorescence microscope observation further revealed that compound II-5 may cause damage to the cell membranes and vacuoles, and the hyphae treated with II-5 could produce obvious and easily observed blue fluorescence. The succinate dehydrogenase (SDH) enzymatic activity and molecular docking simulation indicated that compounds I-3 and I-4 may be potential SDH inhibitors against Alternaria sp.

FUSED HETEROCYCLIC BENZODIAZEPINE DERIVATIVES AND USES THEREOF

-

Page/Page column 130, (2020/05/29)

The present disclosure provides compounds and compositions capable of extending lifespan, and methods of use thereof.

NOVEL BENZODIAZEPINE DERIVATIVES AND USES THEREOF

-

Paragraph 0597-0599, (2019/12/24)

The present disclosure provides compounds and compositions capable of extending lifespan, and methods of use thereof.

SYNTHESIS OF 4-CHLOROKYNURENINES AND INTERMEDIATES

-

Paragraph 48-69, (2019/08/29)

The invention relates to an overall enantio-specific synthesis of 4-chlorokynurenine compounds, in particular L-4-chlorokynurenine, with improved yields. Large-scale syntheses are disclosed. The invention also relates to novel intermediates in the synthes

Enantioselective Anion Recognition by Chiral Halogen-Bonding [2]Rotaxanes

Lim, Jason Y. C.,Marques, Igor,Félix, Vítor,Beer, Paul D.

supporting information, p. 12228 - 12239 (2017/09/12)

The application of chiral interlocked host molecules for discrimination of guest enantiomers has been largely overlooked, which is surprising given their unique three-dimensional binding cavities capable of guest encapsulation. Herein, we combined the stringent linear geometric interaction constraints of halogen bonding (XB), the noncovalent interaction between an electrophilic halogen atom and a Lewis base, with highly preorganized and conformationally restricted chiral cavities of [2]rotaxanes to achieve enantioselective anion recognition. Representing the first detailed investigation of the use of chiral XB rotaxanes for this purpose, extensive 1H NMR binding studies and molecular dynamics (MD) simulation experiments revealed that the chiral rotaxane cavity significantly enhances enantiodiscrimination compared to the non-interlocked free axle and macrocycle components. Furthermore, by examining the enantioselectivities of a family of structurally similar XB [2]rotaxanes containing different combinations of chiral and achiral macrocycle and axle components, the dominant influence of the chiral macrocycle in our rotaxane design for determining the effectiveness of chiral discrimination is demonstrated. MD simulations reveal the crucial geometric roles played by the XB interactions in orientating the bound enantiomeric anion guests for chiral selectivity, as well as the critical importance of the anions' hydration shells in governing binding affinity and enantiodiscrimination.

Improved synthetic routes to the selenocysteine derivatives useful for Boc-based peptide synthesis with benzylic protection on the selenium atom

Shimodaira, Shingo,Iwaoka, Michio

, p. 260 - 271 (2017/03/09)

Selenocysteine (Sec) derivatives, i.e., Boc-Sec(MBn)-OH (1) and Boc-Sec(MPM)-OH (2), which are useful for chemical synthesis of selenopeptides, were obtained from L-serine in five steps with total yields of 73% and 74%, respectively. The enantiomeric excesses were confirmed to be >99% e.e. by optical resolution using a chiral column on HPLC. On the other hand, for the case of a Fmoc-protected Sec derivative, i.e., Fmoc-Sec(MPM)-OH, similar reactions resulted in low yields and partial racemization taking place. [PRESENTED EQUATION]

Synthesis of a Novel Rhizobitoxine-Like Triazole-Containing Amino Acid

Boibessot, Thibaut,Bénimèlis, David,Jean, Marion,Benfodda, Zohra,Meffre, Patrick

supporting information, p. 2685 - 2688 (2016/11/30)

The synthesis of the four stereoisomers of a new 1,2,3-triazole analogue of rhizobitoxine from serine is described. The key step is a Huisgen 1,3-dipolar cycloaddition on an ethynylglycine synthon.

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