7764-95-6

Basic information

• Product Name: BOC-D-Alanine
• Synonyms: BOC-D-ALANINE;BOC-D-ALANINE-OH;BOC-D-ALA-OH;BOC-D-ALA;T-BUTYLOXYCARBONYL-D-ALANINE;N-ALPHA-TERT-BUTYLOXYCARBONYL-D-ALANINE;N-ALPHA-T-BUTOXYCARBONYL-D-ALANINE;N-ALPHA-T-BOC-D-ALA
• CAS NO: 7764-95-6
• Molecular Formula: C₈H₁₅NO₄
• Molecular Weight: 189.21
• EINECS: 1533716-785-6
• Product Categories: Protected Amino Acids;pharmacetical;Amino Acids;Alanine [Ala, A];Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
• Mol File: 7764-95-6.mol
• Article Data: 68

Chemical Properties

• Melting Point: 81-84 °C
• Boiling Point: 324.46°C (rough estimate)
• Flash Point: 147.9 °C
• Appearance: White/Powder
• Density: 1.2321 (rough estimate)
• Vapor Pressure: 6.39E-05mmHg at 25°C
• Refractive Index: 26 ° (C=2, AcOH)
• Storage Temp.: -20°C
• Solubility: Chloroform, DMSO, Methanol
• PKA: 4.02±0.10(Predicted)
• BRN: 2048396
• CAS DataBase Reference: BOC-D-Alanine(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-Alanine(7764-95-6)
• EPA Substance Registry System: BOC-D-Alanine(7764-95-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 7764-95-6(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

N-tert-Boc-D-alanine is an N-Boc-protected form of D-Alanine (A480995). D-Alanine is an amino acid that is commonly found in bacteria, such as Streptococcus faecalis. It is essential for the biosynthesis of peptidoglycan crosslinking sub-units that are used for bacterial cell walls. D-Alanine is also known to cause cytotoxic oxidative stress in brain tumour cells.

InChI:InChI=1/C8H15NO4/c1-5(6(10)11)9-7(12)13-8(2,3)4/h5H,1-4H3,(H,9,12)(H,10,11)/p-1/t5-/m1/s1

Upstream product

• 13303-10-1 tert-Butyl 4-nitrophenyl carbonate 
• 302-72-7 rac-Ala-OH 
• 75-65-0 tert-butyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 3744-87-4 N-t-butyloxycarbonyl-DL-alanine 
• 64-17-5 ethanol 
• 66389-77-3 methyl tert-butyl iminodicarboxylate potassium salt 
• 117049-08-8 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl<(tert-butoxycarbonyl)amino>bromoacetate 
• 117049-10-2 2-tert-Butoxycarbonylamino-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 117681-86-4 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate 
• 4530-20-5 BOC-glycine 
• 909114-65-4 tert-butyl 4,6-dimethoxy-1,3,5-triazinyl carbonate 
• 108811-48-9 tert-butyl (tert-butoxycarbonyl)alaninate 
• 75-44-5 phosgene 

Downstream Products

• 117049-10-2 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (S)-2-<(tert-butoxycarbonyl)amino>propanoate 
• 135214-55-0 Boc-DL-Ala-DL-Ala-OBzl 
• 135112-44-6 Boc-DL-Ala-DL-Ala-DL-Ala-OBzl 
• 158461-97-3 {1-[2-Pyridin-2-yl-5-(2,2,2-trifluoro-ethoxy)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 
• 119289-82-6 {1-[2-Pyridin-3-yl-5-(2,2,2-trifluoro-ethoxy)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 
• 3744-87-4 Boc-(R)-Ala 
• 51814-53-0 N-tert-butoxycarbonyl-L-alanine ethyl ester 
• 95083-33-3 D-(N-tert-butoxycarbonylalanyl)-L-phenylalanine methyl ester 
• 87543-90-6 Boc-D-Ala-Gly-pNA 
• 112037-13-5 (R)-2-((R)-2-tert-Butoxycarbonylamino-propionyloxy)-3-methyl-butyric acid benzyl ester 
• 98688-01-8 Boc-D-Ala-Cys(S-Bzl)-OCH₃ 
• 94476-60-5 2-(4-carboxyphenylsulphonyl)ethyl N-tert-(butoxycarbonyl)-D-alaninate 
• 87363-83-5 Boc-(D)-Ala-ΔBut-(L)-Phe-(L)-Leu-OMe 
• 89545-66-4 Boc-D-Ala-Val-pNA 

Relevant articles and documents

SPIRO-LACTAM COMPOUNDS AND METHODS OF TREATING VIRAL INFECTIONS USING THE SAME

Disclosed are compounds, and pharmaceutically acceptable salts thereof, that can ameliorate or treat a viral infection in a subject in need thereof. The disclosure also includes conjugates of such compounds with a protease.

Cytotoxic activity of synthetic chiral amino acid derivatives

Cancer is a chronic degenerative disease considered one of the most important causes of death worldwide. In this context, a series of dual-protected amino acid derivatives was synthesized and evaluated as potential novel anticancer agents. The 40 derivatives were prepared in up to three reaction steps. The cytotoxic activities were screened in vitro against a panel of tumor and non-tumor cells using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among the synthesized derivatives, three of them showed promising activity against cancer cells with half-maximal inhibitory concentration (IC50) ranging between 1.7-6.1 μM. The most promising derivative, bearing both a lipophilic N-alkyl diamine moiety and a protected amino acid scaffold showed a selectivity index of 3.4 towards tumor cells. The N-alkyl diamine moiety seems to play a crucial role in the enhancement of the anticancer activity. On the other hand, the incorporation of an amino acid scaffold resulted in increase in the selectivity towards cancer cell lines.

Alanine derivative and preparation method and application thereof

The invention discloses an alanine derivative and a preparation method and application thereof. The preparation comprises the following steps: taking biphenylpyridine as a hinge region binding fragment, introducing L-alanine as a flexible linker by adopting a fragment drug design strategy to construct a compound library with kinase inhibitory activity, and discovering a tyrosine kinase inhibitor with Bcr-Abl kinase inhibitory activity through ADP-Glo kinase activity screening. The compound can be used for preparing anti-tumor (chronic myelogenous leukemia) drugs, inhibits kinase activity of Bcr-Abl and Bcr-AblT315I, and has the activity of inhibiting cell proliferation of K562 cells. The introduction of an alanine structure has an important effect on the inhibitory activity of the compound, the structural diversity of the kinase inhibitor can be expanded, and the activity result shows that the structure can be used as a Linker pharmacodynamic fragment of the Bcr-Abl tyrosine kinase inhibitor.