4666-16-4

Basic information

• Product Name: Z-GLU(OTBU)-OSU
• Synonyms: N-CBZ-gamma-tert-butyl-L-glutamic acid hydroxysuccinimide;Z-L-glutamic acid 5-tert-butyl-1-(N-succinimidyl) ester, N-Cbz-γ-t-butyl-L-glutamic acid N-hydroxysuccinimide ester;(S)-5-[(2,5-Dioxopyrrolidin-1-yl)oxy]-5-oxo-4-[[(benzyloxy)carbonyl]amino]pentanoic acid tert-butyl ester;(2S)-2-(benzyloxycarbonylamino)glutaric acid O5-tert-butyl ester O1-succinimido ester;5-O-tert-butyl 1-O-(2,5-dioxopyrrolidin-1-yl) (2S)-2-(phenylmethoxycarbonylamino)pentanedioate;O5-tert-butyl O1-(2,5-dioxopyrrolidin-1-yl) (2S)-2-(phenylmethoxycarbonylamino)pentanedioate;(4S)-5-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-5-oxo-4-[[(phenylmethoxy)carbonyl]amino]pentanoic acid 1,1-dimethylethyl ester;Z-L-Glu(OtBu)-OSu
• CAS NO: 4666-16-4
• Molecular Formula: C₂₁H₂₆N₂O₈
• Molecular Weight: 434.44
• EINECS: 225-111-3
• Product Categories: Amino Acid Derivatives
• Mol File: 4666-16-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 105-107 °C
• Appearance: /
• Density: 1.29 g/cm³
• Refractive Index: 1.556
• Storage Temp.: −20°C
• CAS DataBase Reference: Z-GLU(OTBU)-OSU(CAS DataBase Reference)
• NIST Chemistry Reference: Z-GLU(OTBU)-OSU(4666-16-4)
• EPA Substance Registry System: Z-GLU(OTBU)-OSU(4666-16-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 4666-16-4(Hazardous Substances Data)

Usage

General Description

Z-GLU(OTBU)-OSU is a chemical compound that is commonly used in organic synthesis. It is a derivative of Z-Glutamic acid and is often employed as a building block in the creation of peptides and proteins. The compound contains a protected amino group and carboxylic acid group, making it a versatile tool for constructing various amino acid sequences. Z-GLU(OTBU)-OSU is often utilized in solid-phase peptide synthesis and is known for its stability and compatibility with a wide range of reaction conditions. Its use in the development of new pharmaceuticals and bioactive compounds has made it an important molecule in the field of medicinal chemistry.

InChI:InChI=1/C21H26N2O8/c1-21(2,3)30-18(26)12-9-15(19(27)31-23-16(24)10-11-17(23)25)22-20(28)29-13-14-7-5-4-6-8-14/h4-8,15H,9-13H2,1-3H3,(H,22,28)/t15-/m0/s1

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 3886-08-6 5-tert-butyl N-benzyloxycarbonyl-L-glutamate 

Downstream Products

• 47793-84-0 Z-Glu(OtBu)-Glu(OtBu) 
• 40350-27-4 Z-Glu(OBu^t)-Gly-OBzl 
• 23406-80-6 N^α-Benzyloxycarbonyl-γ-tert.-butyl-Glu-Gly 
• 83537-83-1 Benzyloxycarbonyl-α-L-glutamyl(γ-tert-butyl ester)-valinol 
• 153121-60-9 Z-Glu(OtBu)-Gly-Ala-OH 
• 109794-81-2 Z-L-Glu(OtBu)-L-Lys(Boc)-OH 
• 110484-42-9 Z-Glu(OtBu)-Gln-Glu(OtBu)-OH 
• 63327-72-0 Z-Glu(OBu^t)-Gly-OEt 
• 132307-33-6 Z-Glu(OBu^t)-Arg-Tyr(Bu^t)-Leu-OH 
• 138541-17-0 Z-L-Glu(OtBu)-L-Lys(Boc)-OPh 
• 79432-38-5 Z-Glu(OBu^t)-Ala-Tyr-Ile-Pro-Lys(Boc)-Glu(OBu^t)-Gln-Lys(Boc)-Tyr-Ser-Phe-OBu^t 
• 79432-55-6 Z-Glu(OBu^t)-Ala-Tyr-Ile-Pro-OBu^t 
• 79432-57-8 Z-Glu(OBu^t)-Glu(OBu^t)-Ala-Tyr-Ile-Pro-OBu^t 
• 79432-27-2 Z-Glu(OBu^t)-Gln-Lys(Boc)-Tyr-Ser-Phe-OBu^t 

Relevant articles and documents

Synthesis and In Vitro Neuroprotective Activity of Glycine Analogs of Gk-2 Dimeric Dipeptide Mimetic of Nerve Growth Factor 4th Loop

A dimeric dipeptide mimetic of nerve growth factor (NGF), bis-(N-monosuccinyl-L-glutamyl-L-lysine) hexamethylenediamide (GK-2), was previously developed at V. V. Zakusov State Institute of Pharmacology, activated specific TrkA receptors, and exhibited neuroprotective activity in vitro (10–5 – 10–9 M) and in vivo (0.1 – 10 mg/kg i.p. and p.o.). GK-2 was designed based on the beta-turn (-Asp94-Glu95-Lys96-Gln97-) of the NGF 4th loop and preserved the central dipeptide fragment (-Glu95-Lys96-). The Asp94 residue was replaced by its monosuccinyl bioisostere. The dimeric structure of NGF was reproduced using a bivalent hexamethylenediamine spacer. The structure—activity (neuroprotective) relationship for GK-2 was studied in the present work using a glycine scan, i.e., successive replacement of the peptide side groups by H. The bis-(N-acetyl-L-glutamyl-L-lysine) (GK-2Ac), bis-(N-monosuccinylglycyl-L-lysine) (GK-2-Gly1), and bis-(N-monosuccinyl-L-glutamylglycine) hexamethylenediamides (GK-2-Gly2) were less active with neuroprotective activity in vitro under oxidative stress for HT22 cells at concentrations 10 – 100 times greater than GK-2. The conclusion was drawn that each side radical of GK-2 was important for manifestation of the full neuroprotective activity of dimeric dipeptide GK-2, a mimetic of the NGF 4th loop. However, removal of any of the side radicals would probably not change the active structure of the beta-turn so that the two remaining side radicals should retain the ability to bind to their TrkA subsites. This could explain the retention of neuroprotective activity in the GK-2 glycine analogs.

Electrostatic effects on ion selectivity and rectification in designed ion channel peptides

To help determine how amino acid sequence can influence ionic conduction properties in α-helical structures, we have synthesized and studied three closely related, channel-forming peptides. The sequences are based on a 21-residue amphiphilic Leu-Ser-Ser-Leu-Leu-Ser-Leu heptad repeat motif and differ in having either neutral, negatively, or positively charged N-termini. The channels formed by the neutral peptide are modestly cation selective and exhibit asymmetric current-voltage curves arising from the partial charges at the ends of the α-helix. Addition of a negatively charged Glu residue converted the channel to a completely cation-selective structure and essentially eliminated its rectification. Addition of a positively charged Arg residue near the N-terminus of the peptide reduced this channel's cation selectivity and increased the extent of rectification. These effects on channel ionic conductance can be explained by a theoretical electrostatic model and provide insights into the workings of more complex channel proteins.