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
• Article Data: 6

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

General Description

Z-LYS(Z)-OSU is a chemical compound often used in the synthesis of peptides and proteins. It is a lysine derivative that is commonly used as a reagent for the selective modification of proteins. The Z-OSU (benzyl carbamate) group confers a level of protection and stability to the lysine residue, allowing for controlled and precise modification. Z-LYS(Z)-OSU is particularly useful in chemical biology and medicinal chemistry research, where the specific modification of proteins is important for studying their function and interactions. Z-LYS(Z)-OSU has also been used as a tool in the development of targeted drug delivery systems and protein engineering applications.

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

• 1382783-21-2 N,N'-biscarbobenzyloxy-lisdexamfetamine 
• 1294448-76-2 C₃₀H₃₃N₃O₈ 
• 1258859-55-0 N,N'-biscarbobenzyloxy-chloro-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 
• 137649-64-0 N,N-bis-Cbz-L-lysinol 
• 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 
• 162553-91-5 Bis-N,N'-(Cbz)-L-lysyl-β-benzyl D-threo-β-hydroxyaspartate 
• 109064-89-3 Z-Lys(Z)-Trp(CmES)-OMe 
• 109064-88-2 Z-Lys(Z)-Trp(t-BuS)-OMe 

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

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.

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.