21160-83-8

Basic information

• Product Name: Z-LYS(Z)-OSU
• Synonyms: Z-LYS(Z)-OSU;Z-LYSINE(Z)-OSU;Z-LYS-OSU;na,N-epsilon-di-cbz-L-lysine N-*hydroxysuccinimid;nα,nε-di-z-l-lysine hydroxysuccinimide ester;Z-LYL(Z)-OSU;[(S)-1-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-1,5-pentanediyl]bis(carbamic acid benzyl) ester;Nα,ε-Bis-Z-L-lysineN-hydroxysuccinimide ester99%
• CAS NO: 21160-83-8
• Molecular Formula: C₂₆H₂₉N₃O₈
• Molecular Weight: 511.52
• Mol File: 21160-83-8.mol

Chemical Properties

• Melting Point: 112-113 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.33g/cm³
• Refractive Index: 1.599
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Dioxane (Slightly), Methanol (Slightly, Sonicated), Wate
• PKA: 10.55±0.46(Predicted)
• BRN: 1559792
• CAS DataBase Reference: Z-LYS(Z)-OSU(CAS DataBase Reference)
• NIST Chemistry Reference: Z-LYS(Z)-OSU(21160-83-8)
• EPA Substance Registry System: Z-LYS(Z)-OSU(21160-83-8)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 21160-83-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C26H29N3O8/c30-22-14-15-23(31)29(22)37-24(32)21(28-26(34)36-18-20-11-5-2-6-12-20)13-7-8-16-27-25(33)35-17-19-9-3-1-4-10-19/h1-6,9-12,21H,7-8,13-18H2,(H,27,33)(H,28,34)

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 405-39-0 N,N'-di-[(phenylmethoxy)carbonyl]-L-lysine 

Downstream Products

• 60668-12-4 [[N₂,N₆-bis(benzyloxycarbonyl)-L-lysyl]amino]-methylphosphonic acid 
• 109064-88-2 Z-Lys(Z)-Trp(t-BuS)-OMe 
• 109064-89-3 Z-Lys(Z)-Trp(CmES)-OMe 
• 162553-91-5 Bis-N,N'-(Cbz)-L-lysyl-β-benzyl D-threo-β-hydroxyaspartate 
• 380635-49-4 4,8-bis(benzyloxycarbonyl)-N¹-[N^α,N^ε-bis(benzyloxycarbonyl)-L-lysyl]-N¹²-t-butoxycarbonyl-4,8-diaza-1,12-dodecanediamine 
• 137649-64-0 N,N-bis-Cbz-L-lysinol 
• 1258859-55-0 N,N'-biscarbobenzyloxy-chloro-lisdexamfetamine 
• 1294448-76-2 C₃₀H₃₃N₃O₈ 
• 1382783-21-2 N,N'-biscarbobenzyloxy-lisdexamfetamine 
• 129624-96-0 N¹-(5-{3-[4-((S)-2,6-Diamino-hexanoylamino)-butylamino]-propionylamino}-pentyl)-2-[2-(2,4-dihydroxy-phenyl)-acetylamino]-succinamide 
• 162553-90-4 (Bis-N,N'-(Cbz)-L-lysyl-D-threo-β-hydroxyaspartyl β-benzyl ester)-L-alanyl-D-allo-threonyl-L-alanyl-δ-N-(benzyloxy)-D-cycloornithine 
• 162553-94-8 (Bis-N,N'-(Cbz)-L-lysyl-D-threo-β-hydroxyaspartyl β-benzyl ester)-L-alanyl-D-allo-threonyl-L-alanine tert-butyl ester 
• 1025955-33-2 (2R,3R)-3-((S)-2,6-Bis-benzyloxycarbonylamino-hexanoylamino)-N-{(S)-1-[(1R,2R)-1-((S)-1-carboxy-ethylcarbamoyl)-2-hydroxy-propylcarbamoyl]-ethyl}-2-hydroxy-succinamic acid benzyl ester 
• 138207-66-6 N^α,N^ε-bis(benzyloxycarbonyl)-D-lysinal 

Relevant articles and documents

CONJUGATES COMPRISING CELL-BINDING AGENTS AND CYTOTOXIC AGENTS

The invention provides a branched linker compound with reactive moieties for forming covalent bonds with multiple cytotoxic agents (drugs) and/or a cell-binding agent (CBA); a cytotoxic compound comprising a branched linker moiety with a reactive group fo

Direct PCR amplification of various modified DNAs having amino acids: Convenient preparation of DNA libraries with high-potential activities for in vitro selection

We synthesized modified 2′-deoxyuridine triphosphates bearing amino acids at the C5 position and investigated their substrate properties for KOD Dash DNA polymerase during polymerase chain reaction (PCR). PCR using C5-modified dUTP having an amino acyl group (arginyl, histidyl, lysyl, phenylalanyl, tryptophanyl, leucyl, prolyl, glutaminyl, seryl, O-benzyl seryl or threonyl group) gave the corresponding full-length PCR products in good yield. Although dUTP analogues bearing aspartyl, glutamyl or cysteinyl were found to be poor substrates for PCR catalyzed by KOD Dash DNA polymerase, optimization of the reaction conditions resulted in substantial generation of full-length product. In the case of reaction using dUTP analogue having a cysteinyl group, addition of a reducing agent improved the reaction yield. Thus, PCRs using KOD Dash DNA polymerase together with amino acyl dUTP provide convenient and efficient preparation of various modified DNA libraries with potential protein-like activities.

Procedure for the oxidation of β-amino alcohols to α-amino aldehydes

A novel procedure for the mild oxidation of β-amino alcohols to α-amino aldehydes using commercially available manganese(IV) oxide is reported. There are several important advantages of the new method, such as high enantiopurity of the reaction and the absence of either over-oxidation or any reaction by-products during the process. A number of N-protected L-α-amino aldehydes was obtained. All new compounds were characterized by their NMR spectra and optical rotation data. Georg Thieme Verlag Stuttgart.

Synthesis of the Peptide Fragment of Pseudobactin

Synthesis of the peptide fragment, L-Lys-D-threo-β-OH-Asp-L-Ala-D-allo-Thr-L-Ala-N-OH-D-cOrn, of pseudobactin (2) is reported.By utilizing 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) as a coupling reagent, peptide bonds were constructed without requiring protection of hydroxyl groups.To access the D-allo-Thr residue in the peptide fragment of pseudobactin, the Thr residue in N-Cbz-L-Ala-D-Thr-L-Ala-O-t-Bu (4b) was converted to a peptidyl oxazoline using Burgess' reagent.Hydrolysis of the oxazoline with 1 N HCl followed by base-catalyzed acyl migration then provided the D-allo-Thr analog 4a.

Analgesic Dipeptide Derivatives. 3. Synthesis and Structure-Activity Relationships of o-Nitrophenyl-Modified Analogues of the Analgesic Compound H-Lys-Trp(NPS)-OMe

A series of analogues of the analgesic dipeptide derivative H-Lys-Trp(NPS)-OMe has been designed to determine the influence of the (2-nitrophenyl)sulfenyl (NPS)moiety on the activity.The syntheses and antinociceptive effects of these analogues of general formula H-Lys-Trp(R)-OMe sulfenyl (AacCmES) (13); R = sulfenyl (AacPS) (17); R = tert-butylsulfenyl (t-BuS) (23); R = (2-carbomethoxyethyl)sulfenyl (CmES) (24)> are described.Reaction of Z-Lys(Z)-Trp-OMe (3) with PS-, CmPS-, pNPS-, DNPS-, and AacCmES-Cl afforded the corresponding 2-(sulfenyl)tryptophan derivatives, which on treatment with boron-tris(trifluoroacetate)/trifluoroacetic acid or trimethylsilyl iodide in acetonitrile (Me3SiI/CH3CN) provided 9-13, respectively.Sulfenylation of 3 with NPS-Cl gave Z-Lys(Z)-Trp(NPS)-OMe, which, on catalytic hydrogenation of the nitro group using 10percent Pd/C followed by acetylation of the resulting amino function and removal of the protecting Z group, gave 17.Condensation of 2-(ter-butylsulfenyl)- and 2-tryptophan methyl ester, obtained by reaction of methyl 3a -hydroxy-1,2,3,3a,8,8a-hexahydropyrroloindole-2-carboxylate with the corresponding thiol, with Z-Lys(Z)-OSu afforded Z-Lys(Z)-Trp(t-BuS)-OMe and Z-Lys(Z)-Trp(CmES)-OMe, which on treatment with Me3SiI/CH3CN provided 23 and 24, respectively.Intracerebroventricular administration of 10 elicited a naloxone-reversible antinociceptive effect in mice similar to that of H-Lys-Trp(NPS)-OMe.No analgesia was however found with the phenylsulfenyl or acyclic sulfenyl substituted dipeptides 9, 11, and 17 or 13, 23, and 24.The Trp(DNPS)-containing analogue was neurotoxic.Structure-activity studies indicate that the role of the NPS and CmPS moieties could be related to the adoption of a preferential active conformation.

Peptide Synthesis by Prior Thiol Capture. 4. Amide Bond Formation: The Effect of Side-Chain Substituent on the Rates of Intramolecular O,N-Acyl Transfer

The effects of varying steric bulk of the side chain substituent of the acylating agent on rate of the amide bond forming step of the dibenzofuran-based thiol capture strategy were determined from rates of intramolecular isomerization of methyl S-4-(N-be