82869-11-2

Basic information

• Product Name: Carbamic acid, [1-(chloroacetyl)-5-[[(phenylmethoxy)carbonyl]amino]pentyl]-, 1,1-dimethylethyl ester, (S)-
• CAS NO: 82869-11-2
• Molecular Formula: C20H29ClN2O5
• Molecular Weight: 412.914
• Mol File: 82869-11-2.mol

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [1-(chloroacetyl)-5-[[(phenylmethoxy)carbonyl]amino]pentyl]-, 1,1-dimethylethyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [1-(chloroacetyl)-5-[[(phenylmethoxy)carbonyl]amino]pentyl]-, 1,1-dimethylethyl ester, (S)-(82869-11-2)
• EPA Substance Registry System: Carbamic acid, [1-(chloroacetyl)-5-[[(phenylmethoxy)carbonyl]amino]pentyl]-, 1,1-dimethylethyl ester, (S)-(82869-11-2)

Safety Data

• Hazardous Substances Data: 82869-11-2(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 2389-45-9 Boc-Lys(Z)-OH 
• 172833-14-6 ((S)-5-tert-Butoxycarbonylamino-7-diazo-6-oxo-heptyl)-carbamic acid benzyl ester 

Downstream Products

• 138848-96-1 Boc-Lys(Z)-4-benzoylanilinomethyl ketone 
• 773024-34-3 [(S)-7-(4-Benzoyl-phenoxy)-5-tert-butoxycarbonylamino-6-oxo-heptyl]-carbamic acid benzyl ester 
• 179675-13-9 Boc-L-Lys(Z)OH 
• 52780-87-7 HCl*H-Lys(Z)-CH₂Cl 
• 882173-21-9 ((S)-5-Benzoylamino-7-chloro-6-oxo-heptyl)-carbamic acid benzyl ester 
• 882173-17-3 [(S)-7-Chloro-6-oxo-5-(3-phenyl-propionylamino)-heptyl]-carbamic acid benzyl ester 
• 882173-18-4 {(S)-7-Chloro-5-[3-(4-hydroxy-phenyl)-propionylamino]-6-oxo-heptyl}-carbamic acid benzyl ester 
• 882173-19-5 Z-GABA-Lys(Z)-CH₂Cl 
• 882173-20-8 ((S)-5-{2-[4-(Benzyloxycarbonylamino-methyl)-phenyl]-acetylamino}-7-chloro-6-oxo-heptyl)-carbamic acid benzyl ester 
• 882173-24-2 ((S)-7-Chloro-5-{(S)-2-[(naphthalene-2-carbonyl)-amino]-3-phenyl-propionylamino}-6-oxo-heptyl)-carbamic acid benzyl ester 
• 882173-22-0 BocPhe-Phe-Lys(Z)-CH₂Cl 
• 52780-89-9 Boc-Phe-Lys(Z)-CH₂Cl 
• 234449-96-8 6-(4-benzyloxycarbonylaminobutyl)-3-(2-benzyloxycarbonylethyl)-5-methyl-2(1H)-pyrazinone 

Relevant articles and documents

Exploring the Sn binding pockets in gingipains by newly developed inhibitors: Structure-based design, chemistry, and activity

Arg-gingipains (Rgps) and Lys-gingipain (Kgp) are cysteine proteinases secreted by Porphyromonas gingivalis, the major pathogen implicated in periodontal disease. Gingipains are essential to the bacterium for its virulence and survival, and development of inhibitors targeting these proteins provides an approach to treat periodontal diseases. Here, we present the first example of structure-based design of gingipains inhibitors, with the use of the crystal structure of RgpB and the homology model of Kgp. Chloromethyl ketones were selected as suitable compounds to explore the specificity of the Sn binding region of both enzymes. Three series of inhibitors bearing Arg or Lys at P1 and different substituents at P2 and P3 were designed, synthesized, and tested. High potency (kobs/[I] ～ 107 M-1 s -1) was achieved for small ligands, such as the dipeptide analogues. The detailed analysis of Sn binding pockets revealed the molecular basis of inhibitory affinity and provided insight into the structure-activity relationship.