32886-55-8

Basic information

• Product Name: BOC-GLU(OTBU)-OSU
• Synonyms: BOC-GLUTAMIC ACID(OTBU)-OSU;BOC-GLU(OTBU)-OSU;BOC-L-GLUTAMIC ACID-GAMMA-T-BUTYL-ALPHA-HYDROXYSUCCINIMIDE DIESTER;BOC-L-GLUTAMIC ACID-GAMMA-T-BUTYL ESTER ALPHA-N-HYDROXYSUCCINIMIDE ESTER;N-ALPHA-T-BOC-L-GLUTAMIC ACID GAMMA-T-BUTYL ESTER N-HYDROXYSUCCINIMIDE ESTER;N-ALPHA-T-BOC-L-GLUTATMIC ACID GAMMA-T-BUTYL ESTER N-HYDROXYSUCCINIMIDE ESTER;BOC-L-GLUTAMIC ACID-Y-T-BUTYL-A-HYDROXYSUCCINIMID-DIESTER;(S)-5-tert-Butyl 1-(2,5-dioxopyrrolidin-1-yl) 2-((tert-butoxycarbonyl)aMino)pentanedioate
• CAS NO: 32886-55-8
• Molecular Formula: C₁₈H₂₈N₂O₈
• Molecular Weight: 400.42
• Mol File: 32886-55-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: -15°C
• CAS DataBase Reference: BOC-GLU(OTBU)-OSU(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-GLU(OTBU)-OSU(32886-55-8)
• EPA Substance Registry System: BOC-GLU(OTBU)-OSU(32886-55-8)

Safety Data

• Hazardous Substances Data: 32886-55-8(Hazardous Substances Data)

Usage

General Description

BOC-GLU(OTBU)-OSU is a chemical compound used in peptide synthesis. It is an amino acid derivative where BOC (tert-butyloxycarbonyl) and OTBU (tert-butyl) are protective groups that prevent unwanted side reactions during the synthesis process. These protective groups can be selectively removed afterwards. OSU, in the name, signifies the place where the compound was first synthesized. The compound plays an essential role in biochemical research and peptide-related drug development. The GLU in the name refers to Glutamic acid, which is one of the 20 amino acids used in forming proteins.

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 13726-84-6 Boc-Glu(OtBu)-OH 

Downstream Products

• 192052-54-3 (S)-2-[(S)-2-((S)-4-tert-Butoxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoic acid benzyl ester 
• 192052-55-4 (S)-2-[(S)-2-((S)-4-tert-Butoxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoic acid 
• 192052-56-5 (S)-4-tert-Butoxycarbonylamino-4-{(S)-2-(4-hydroxy-phenyl)-1-[(S)-3-methyl-1-(morpholine-4-carbonyl)-butylcarbamoyl]-ethylcarbamoyl}-butyric acid tert-butyl ester 
• 192052-58-7 4-{4-[(S)-2-((S)-1-Benzyloxycarbonyl-3-methyl-butylcarbamoyl)-2-((S)-4-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-ethyl]-phenoxysulfonyl}-benzoic acid 
• 192052-62-3 4-{4-[(S)-2-((S)-1-Benzyloxycarbonyl-3-methyl-butylcarbamoyl)-2-((S)-4-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-ethyl]-phenoxysulfonyl}-2-hydroxy-benzoic acid 
• 192052-65-6 C₅₆H₇₀N₈O₁₆S 
• 192052-72-5 Boc-Glu(O^tBu)-Tyr[CO(CH₂)4CO-bzoc⁶A(=CMe₂)]-Leu-morpholine 
• 1239116-67-6 (S)-Boc-Glu(Ot-Bu)-NHBn 
• 1009103-03-0 C₃₈H₅₀ClN₅O₁₁S 
• 1260020-43-6 N-Boc-(S)-glutamic acid (tert-butyl ester)-mexiletine 
• 1260020-44-7 mexiletine-(S)-glutamic acid amide hydrochloride 

Relevant articles and documents

Ynamide-Mediated Thiopeptide Synthesis

Exploration of the full potential of thioamide substitution as a tool in the chemical biology of peptides and proteins has been hampered by insufficient synthetic strategies for the site-specific introduction of a thioamide bond into a peptide backbone. A novel ynamide-mediated two-step strategy for thiopeptide bond formation with readily available monothiocarboxylic acids as thioacyl donors is described. The α-thioacyloxyenamide intermediates formed from the ynamides and monothiocarboxylic acids can be purified, characterized, and stored. The balance between their activity and stability enables them to act as effective thioacylating reagents to afford thiopeptide bonds under mild reaction conditions. Amino acid functional groups such as OH, CONH2, and indole NH groups need not be protected during thiopeptide synthesis. The modular nature of this strategy enables the site-specific incorporation of a thioamide bond into peptide backbones in both solution and the solid phase.