69677-02-7

Usage

Uses

N,N''-Dibenzyloxycarbonyl-D-lysine

InChI:InChI=1/C22H26N2O6/c25-20(26)19(24-22(28)30-16-18-11-5-2-6-12-18)13-7-8-14-23-21(27)29-15-17-9-3-1-4-10-17/h1-6,9-12,19H,7-8,13-16H2,(H,23,27)(H,24,28)(H,25,26)/t19-/m1/s1

Upstream product

• 923-27-3 D-lysine 
• 501-53-1 benzyl chloroformate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

• 1375013-89-0 N₂,N₆-bis[(benzyloxy)carbonyl]-D-lysyl-N₆-[(benzyloxy)carbonyl]-N-(4-[(2-tert-butyl-6-methoxyquinolin-8-yl)amino]pentyl)-D-lysinamide 
• 1295647-53-8 [(R)-5-benzyloxycarbonylamino-5-fluorocarbonylpentyl]carbamic acid benzyl ester 
• 69677-06-1 N,N'-Dibenzyloxycarbonyl-(R)-β-homolysin 
• 69677-07-2 [N'-((R)-3,7-Bis-benzyloxycarbonylamino-heptanoyl)-N-methyl-hydrazino]-acetic acid ethyl ester 
• 69677-08-3 [N'-((R)-3,7-Bis-benzyloxycarbonylamino-heptanoyl)-N-methyl-hydrazino]-acetic acid 
• 97485-07-9 N^α,N^ε-Bis(benzyloxycarbonyl)-D-lysyl-N^ε-(benzyloxycarbonyl)-D-lysine Methyl Ester 
• 925934-33-4 (R)-{5-benzyloxycarbonylamino-1-[4-(2-tert-butyl-6-methoxy-8-quinolylamino)pentylcarbamoyl]pentyl}carbamic acid benzyl ester 
• 925934-78-7 (R)-{5-benzyloxycarbonylamino-1-[4-(4-ethyl-6-methoxy-5-pentyloxy-8-quinolylamino)pentylcarbamoyl]pentyl}carbamic acid benzyl ester 
• 97485-06-8 (Z)-D-Lys(Z)-OPcp 
• 69677-05-0 N,N'-Dibenzyloxycarbonyl-(R)-β-homolysinmethylester 

Relevant academic research and scientific papers

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.

Chemical dynamic kinetic resolution and S/R interconversion of unprotected α-amino acids

Reported herein is the first purely chemical method for the dynamic kinetic resolution (DKR) of unprotected racemic α-amino acids (α-AAs), a method which can rival the economic efficiency of the enzymatic reactions. The DKR reaction principle can be readily applied for S/R interconversions of α-AAs, the methodological versatility of which is unmatched by biocatalytic approaches. The presented process features a virtually complete stereochemical outcome, fully recyclable source of chirality, and operationally simple and convenient reaction conditions, thus allowing its ready scalability. A quite unique and novel mode of the thermodynamic control over the stereochemical outcome, including an exciting interplay between axial, helical, and central elements of chirality is proposed. A new player for DKR: Dynamic kinetic resolution of α-amino acids has been achieved upon complexation with nickel(II) and a chiral ligand derived from optically active bis(naphthyl)amine under thermodynamic control, thus affording excellent diastereoselectivities and chemical yields. The S to R interconversion of α-amino acids is also described.

Differentiation Among the Four Diastereomers of Benzyloxycarbonyl-protected γ-Hydroxyornithine in Negative-ion Fast Atom Bombardment Mass Spectrometry

Discrimination among the four γ-hydroxyornithine diastereomers was studied by fast atom bombardment mass spectrometry (FABMS).It is impossible to distinguish among the four diastereomers of this amino acid by positive- and negative-ion FAB and collisionally activated dissociation MS, but benzyloxycarbonyl group protection of the α- and δ-amino groups in γ-hydroxyornithine allows differentiation among the diastereomers in negative-ion FABMS.The negative-ion mass spectra of benzyloxycarbonyl-protected γ-hydroxyornithine diastereomers showed differences among the abundances of the molecule ion (-), the dehydrated ion (-) due to the loss of the γ-hydroxyl group and the fragment ions formed from both (-) and (-) ions.On the other hand, no difference was found between the fragmentations of the benzyloxycarbonyl-protected enantiomers of ornithine in negative-ion FABMS.These results indicate that the orientation of the γ-hydroxyl group and the existence of two benzene rings in the benzyloxycarbonyl group are important factors which are responsible for the fragmentations of the four benzyloxycarbonyl-protected γ-hydroxyornithine diastereomers in negative-ion FABMS.These studies also showed that the negative-ion FABMS for benzyloxycarbonyl-protected γ-hydroxyornithine diastereomers is a useful method for determining the configuration of each diastereomer of γ-hydroxyornithine.