16937-99-8

Basic information

• Product Name: BOC-D-Leucine monohydrate
• Synonyms: N-(TERT-BUTOXYCARBONYL)-D-LEUCINE;N-ALPHA-T-BOC-D-LEUCINE;BOC-D-LEU-OH;BOC-D-LEUCINE;L-LEUCINE-5,5,5-D3, N-T-BOC DERIV.H20 98;N-T-BOC-D-LEUCINE;N-TERT-BUTOXYCARBONYL-D-LEUCINE 1-HYDRATE;Boc-D-Leu-OH hydrate
• CAS NO: 16937-99-8
• Molecular Formula: C₁₁H₂₁NO₄
• Molecular Weight: 249.3
• EINECS: 1312995-182-4
• Product Categories: Amino Acids;Leucine [Leu, L];Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
• Mol File: 16937-99-8.mol
• Article Data: 19

Chemical Properties

• Melting Point: 85-87 °C(lit.)
• Boiling Point: 356 °C at 760 mmHg
• Flash Point: 169.1 °C
• Appearance: white fine crystals
• Density: 1.061 g/cm3
• Vapor Pressure: 4.98E-06mmHg at 25°C
• Refractive Index: 25 ° (C=2, AcOH)
• Storage Temp.: −20°C
• Solubility: Acetic Acid (Sparingly), DMSO (Slightly), Methanol (Slightly)
• PKA: 4.02±0.21(Predicted)
• BRN: 2331060
• CAS DataBase Reference: BOC-D-Leucine monohydrate(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-Leucine monohydrate(16937-99-8)
• EPA Substance Registry System: BOC-D-Leucine monohydrate(16937-99-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 16937-99-8(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline

Uses

N-Boc-D-leucine is an N-Boc-protected form of D-Leucine (L330150). D-Leucine is an unnatural isomer of L-Leucine (L330110) that acts as an auto-inhibitor of lactic streptococci in culture. D-Leucine causes analgesia in humans and also exhibits inhibitory activity in bacterial cell cultures.

InChI:InChI=1/C11H21NO4.H2O/c1-7(2)6-8(9(13)14)12-10(15)16-11(3,4)5;/h7-8H,6H2,1-5H3,(H,12,15)(H,13,14);1H2/t8-;/m1./s1

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 328-38-1 (R)-leucine 
• 19792-08-6 p-nitrophenyl-N-(t-butoxycarbonyl)-D-leucinate 
• 41840-28-2 S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine 
• 54594-06-8 D-allylglycine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 106930-51-2 tert-butyl [(2R)-1-hydroxy-4-methylpentan-2-yl]carbamate 
• 756498-96-1 ethyl N-tert-butyloxycarbonyl-2-amino-4-methyl-pentanoate 
• 170642-23-6 (S,S)-pseudoephedrine D-allylglycinamide 
• 129505-08-4 (2R,2'R)-N-<2'-(hydroxyamino)-4'-methylpentanoyl>bornane-10,2-sultam 
• 129568-83-8 (2R,2'R)-N-(2'-amino-4'-methylpentanoyl)bornane-10,2-sultam 
• 129505-02-8 (2R)-N-(4-methylpentanoyl)bornane-10,2-sultam 
• 38136-29-7 4-methylvaleroyl chloride 
• 219819-68-8 tert-butyl (R)-2-(((tert-butyldimethylsilyl)oxy)-methyl)aziridine-1-carboxylate 

Downstream Products

• 116300-00-6 1-diazo-3(R)-<<(1,1-dimethylethoxy)carbonyl>amino>-5-methyl-2-hexanone 
• 73401-70-4 Boc-Leu-OMPA 
• 78834-53-4 BOC-D-Leu-L-Val-pNA 
• 140834-91-9 Boc-D-Leu-Phe-OBzl 
• 137022-74-3 Boc-D-Leu-Gly-NHOBzl 
• 137029-92-6 [(R)-1-((S)-1-Benzyl-2-oxo-2-piperidin-1-yl-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester 
• 137005-62-0 {(R)-1-[(S)-1-Benzyl-2-oxo-2-(4-phenyl-piperidin-1-yl)-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester 
• 137005-63-1 {(R)-1-[(S)-1-Benzyl-2-oxo-2-(4-phenyl-piperazin-1-yl)-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester 
• 137005-64-2 ((R)-1-{(S)-2-[4-(4-Acetyl-phenyl)-piperazin-1-yl]-1-benzyl-2-oxo-ethylcarbamoyl}-3-methyl-butyl)-carbamic acid tert-butyl ester 
• 137005-65-3 {(R)-1-[(S)-2-(4-Benzo[1,3]dioxol-5-ylmethyl-piperazin-1-yl)-1-benzyl-2-oxo-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester 
• 77302-94-4 (S)-2-{(S)-4-Benzyloxycarbonyl-2-[(S)-4-benzyloxycarbonyl-2-((R)-2-tert-butoxycarbonylamino-4-methyl-pentanoylamino)-butyrylamino]-butyrylamino}-4-methyl-pentanoic acid methyl ester 
• 77302-93-3 (R)-2-{(S)-4-Benzyloxycarbonyl-2-[(S)-4-benzyloxycarbonyl-2-((R)-2-tert-butoxycarbonylamino-4-methyl-pentanoylamino)-butyrylamino]-butyrylamino}-4-methyl-pentanoic acid methyl ester 
• 78834-52-3 BOC-D-Leu-D-Val-pNA 
• 99242-14-5 Boc-D-Leu-D-Phe-pNA 

Relevant articles and documents

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D-amino acid position influences the anticancer activity of galaxamide analogs: An apoptotic mechanism study

Galaxamide, an extract from Galaxaura filamentosa, is a cyclic pentapeptide containing five L-leucines. Due to the particular cyclic structure and the excellent anticancer activity, synthesis of Galaxamide and its analogs and their subsequent bio-applications have attracted great attention. In the present work, we synthesized six Galaxamide analogs by replacing one of the L-leucines with phenylalanine and varying the D-amino acid position. The anticancer effect of the synthesized Galaxamide analogs was tested against four in vitro human cancer cell lines, human hepatocellular cells (HepG2), human breast cancer cell (MCF-7), human breast adenocarcinoma cells (MDA-MB-435) and a human cervical carcinoma cell line (Hela). Results showed that Galaxamide analogs with differentD-amino acid positions displayed distinct anticancer potential. The Galaxamide analog containing D-amino acid at position 5 (Analog-6) presented the strongest anticancer activity. The mechanism study revealed that Analog-6 could cause the early apoptosis of HepG2 cells by inhibiting their growth in the sub-G1 stage of the cell cycle and induce the chromatin condensation and fragmentation, which can be seen as 68% of HepG2 cells inhibited in the sub-G1 stage. Moreover, a mitochondria-mediated pathway was found to be involved in the apoptotic process of Analog-6 on HepG2 cells.

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