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

Description

BOC-D-Leucine monohydrate is an N-Boc-protected form of D-Leucine, an unnatural isomer of L-Leucine. It is a white crystalline substance that acts as an auto-inhibitor of lactic streptococci in culture and has potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
BOC-D-Leucine monohydrate is used as an analgesic agent for its ability to cause analgesia in humans. It is also used as an inhibitor in bacterial cell cultures due to its inhibitory activity.
Used in Chemical Synthesis:
BOC-D-Leucine monohydrate is used as a protected amino acid in the synthesis of peptides and other organic compounds, where the N-Boc group can be selectively removed to reveal the free D-Leucine.
Used in Research and Development:
BOC-D-Leucine monohydrate is used as a research compound for studying the properties and applications of D-Leucine and its derivatives, as well as for investigating the mechanisms of auto-inhibition in lactic streptococci.

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

• 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 
• 24424-99-5 di-tert-butyl dicarbonate 
• 38136-29-7 4-methylvaleroyl chloride 
• 170642-23-6 (S,S)-pseudoephedrine D-allylglycinamide 
• 219819-68-8 tert-butyl (R)-2-(((tert-butyldimethylsilyl)oxy)-methyl)aziridine-1-carboxylate 
• 152491-85-5 (R)-[1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester 
• 126645-26-9 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 328-38-1 (R)-leucine 
• 73371-96-7 2-<<(tert-butoxycarbonyl)oxy>imino>-2-phenylacetonitrile 
• 756498-96-1 ethyl N-tert-butyloxycarbonyl-2-amino-4-methyl-pentanoate 
• 69805-63-6 methyl 2-((tert-butoxycarbonyl)amino)-4-methylpentanoate 

Downstream Products

• 158804-50-3 Boc-D-leucine benzyl ester 
• 878270-17-8 N-(tert-butyloxycarbonyl)-D-leucyl-(S-3,5-diiodo-4-methoxyphenylglycine) methyl ester 
• 672961-96-5 (+)-(R)-N²-(tert-butoxycarbonyl)-N¹-(2,6-dimethylphenyl)leucinamide 
• 504412-16-2 (S)-2-{(4R,7S)-7-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentyl]-2,2-dimethyl-4,7-dihydro-[1,3,2]dioxasilepin-4-yl}-thiopropionic acid S-benzyl ester 
• 504412-86-6 (Z)-(2S,3R,6S,8R)-8-(9H-Fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2,10-dimethyl-undec-4-enethioic acid S-benzyl ester 

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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