55878-47-2

Basic information

• Product Name: BOC-D-LYS(Z)-OH
• Synonyms: BOC-N-EPSILON-Z-D-LYSINE;BOC-D-LYSINE(CBZ);BOC-D-LYSINE(Z)-OH;N-ALPHA-BUTOXYCARBONYL-N-EPSILON-CARBOBENZOXY-D-LYSINE;N-ALPHA-BOC-N-EPSILON-BENZYLOXYCARBONYL-D-LYSINE;N-ALPHA-TERT-BUTYLOXYCARBONYL-N-EPSILON-BENZYLOXYCARBONYL-D-LYSINE;N2-[(1,1-Dimethylethoxy)Carbonyl]-N6-[(Phenylmethoxy)Carbonyl]-D-Lysine;Nalpha-Boc-Nepsilon-Z-D-lysine
• CAS NO: 55878-47-2
• Molecular Formula: C₁₉H₂₈N₂O₆
• Molecular Weight: 380.44
• Mol File: 55878-47-2.mol

Chemical Properties

• Boiling Point: 587°Cat760mmHg
• Flash Point: 308.8°C
• Appearance: /
• Density: 1.176g/cm³
• Storage Temp.: Store at RT.
• PKA: 3.99±0.21(Predicted)
• CAS DataBase Reference: BOC-D-LYS(Z)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-LYS(Z)-OH(55878-47-2)
• EPA Substance Registry System: BOC-D-LYS(Z)-OH(55878-47-2)

Safety Data

• Hazardous Substances Data: 55878-47-2(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 32302-83-3 N-ε-benzyloxycarbonyl lysine 
• 34404-32-5 (R)-2-amino-6-(((benzyloxy)carbonyl)amino)hexanoic acid 
• 7274-88-6 D-lysine hydrochloride 
• 501-53-1 benzyl chloroformate 
• 923-27-3 D-lysine 
• 106719-44-2 Boc-D-Lys-OH 

Downstream Products

• 218927-55-0 (S)-3-[3-((S)-2-Acetylamino-2-benzyloxycarbonyl-ethyl)-phenyl]-2-((S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-propionic acid methyl ester 
• 172833-14-6 ((S)-5-tert-Butoxycarbonylamino-7-diazo-6-oxo-heptyl)-carbamic acid benzyl ester 
• 693222-16-1 [5-(5-benzyloxycarbonylamino-1-chloroacetyl-pentylcarbamoyl)-5-tert-butoxycarbonylamino-pentyl]-carbamic acid benzyl ester 
• 77004-72-9 Boc-rac-Lys(Z)-OtBu 

Relevant articles and documents

DRUG-LOADED EMULSION

The present invention relates to a drug-loaded emulsion, comprising a modified hydrophobic excipient having the following formula, a hydrophobic drug and a surfactant: where R is a hydrophobic natural compound or a hydrophobic synthetic compound with one to three hydroxyl groups (n=1-3); and R1 is an α-amino protecting group, and R2 is an amino acid side chain, wherein, when m=0, R is reacted with an amino acid derivative with a protecting group by esterification to form a hydrophobic excipient carrying the amino acid derivative with a protecting group; or when m=1, R is firstly introduced with an amino acid linking arm of different chain lengths (l=1, 2, 4, 6) via an ester group, and then introduced with an amino acid derivative with a protecting group.

Enantioselective Deaminative Alkylation of Amino Acid Derivatives with Unactivated Olefins

Herein, we report the first Ni-catalyzed enantioselective deaminative alkylation of amino acid and peptide derivatives with unactivated olefins. Key for success was the discovery of a new sterically encumbered bis(oxazoline) ligand backbone, thus offering a de novo technology for accessing enantioenriched sp3-sp3 linkages via sp3 C-N functionalization. Our protocol is distinguished by its broad scope and generality across a wide number of counterparts, even in the context of late-stage functionalization. In addition, an enantioselective deaminative remote hydroalkylation reaction of unactivated internal olefins is within reach, thus providing a useful entry point for forging enantioenriched sp3-sp3 centers at remote sp3 C-H sites.

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Discovery and Characterization of Biased Allosteric Agonists of the Chemokine Receptor CXCR3

In this work we report a design, synthesis, and detailed functional characterization of unique strongly biased allosteric agonists of CXCR3 that contain tetrahydroisoquinoline carboxamide cores. Compound 11 (FAUC1036) is the first strongly biased allosteric agonist of CXCR3 that selectively induces weak chemotaxis and leads to receptor internalization and the β-arrestin 2 recruitment with potency comparable to that of the chemokine CXCL11 without any activation of G proteins. A subtle structural change (addition of a methoxy group, 14 (FAUC1104)) led to a contrasting biased allosteric partial agonist that activated solely G proteins, induced chemotaxis, but failed to induce receptor internalization or β-arrestin 2 recruitment. Concomitant structure-activity relationship studies indicated very steep structure-activity relationships, which steer the ligand bias between the β-arrestin 2 and G protein pathway. Overall, the information presented provides a powerful platform for further development and rational design of strongly biased allosteric agonists of CXCR3.

Concise total synthesis of aplysinellamides A and B

Concise and efficient total syntheses of bromotyrosine-derived metabolites aplysinellamides A and B, isolated from Australian marine sponge Aplysinella sp., have been accomplished in seven steps. A condensation between cinnamic acid and Boc-D-lysine methyl ester was applied to form the amide skeleton as a key step.

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