861658-15-3

Basic information

• Product Name: 1,5-dimethyl 2-[(t-butoxycarbonyl)amino]pentanedioate
• CAS NO: 861658-15-3
• Molecular Weight: 275.302
• Mol File: 861658-15-3.mol
• Article Data: 71

Chemical Properties

• CAS DataBase Reference: 1,5-dimethyl 2-[(t-butoxycarbonyl)amino]pentanedioate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-dimethyl 2-[(t-butoxycarbonyl)amino]pentanedioate(861658-15-3)
• EPA Substance Registry System: 1,5-dimethyl 2-[(t-butoxycarbonyl)amino]pentanedioate(861658-15-3)

Safety Data

• Hazardous Substances Data: 861658-15-3(Hazardous Substances Data)

Usage

Chemical class

Amino dicarboxylic acids and derivatives

Molecular weight

229.29 g/mol

Appearance

Colorless to pale yellow solid or liquid

Solubility

Soluble in organic solvents such as ethanol, methanol, and acetonitrile

Melting point

Not readily available, but likely to be low due to the presence of flexible carbon chain

Boiling point

Not readily available, but likely to be relatively high due to the presence of multiple functional groups

Density

Not readily available, but likely to be less than 1 g/cm3 due to the presence of a carbon chain

Functional groups

Carboxylic acid, amino, and t-butoxycarbonyl protecting group

Reactivity

Reacts with various reagents to form peptide and protein derivatives

Applications

Organic synthesis
Preparation of peptide and protein derivatives
Production of pharmaceuticals, agrochemicals, and other fine chemicals
Potential applications in medicine and biochemistry due to structural similarity to natural amino acids and ability to modify peptide and protein properties

Safety

Handle with care, as it may be harmful if inhaled, ingested, or if it comes into contact with the skin

Storage

Store in a cool, dry, and well-ventilated area, away from heat, sparks, and open flames

Stability

Stable under normal conditions, but may decompose upon exposure to heat, light, or moisture

Regulatory status

Not readily available, but it may be subject to specific regulations depending on its intended use and concentration in a given product.

Upstream product

• 67-56-1 methanol 
• 56-86-0 L-glutamic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 6893-26-1 D-Glutamic acid 
• 75-77-4 chloro-trimethyl-silane 
• 2419-94-5 Boc-Glu 
• 74-88-4 methyl iodide 
• 6525-53-7 L-glutamic acid dimethyl ester 
• 13726-85-7 Boc-Gln-OH 
• 56-85-9 L-glutamine 
• 67436-17-3 dimethyl (S)-N-(benzyloxycarbonyl)glutamate 
• 23150-65-4 L-glutamic dimethyl ester hydrochloride 
• 500143-66-8 dimethyl (2S)-2-{N-[(tert-butoxy)carbonyl]benzyloxycarbonylamino}pentane-1,5-dioate 
• 206128-03-2 (S)-dimethyl 2-(bis(tert-butoxycarbonyl)amino)pentanedioate 

Downstream Products

• 334618-23-4 3-(R)-aminopiperidine dihydrochloride 
• 72086-72-7 N-tert-butoxycarbonylglutamic acid methyl ester 

Relevant articles and documents

[1,2] Boc migration during pyroglutamate alkylations

Treatment of N-Boc protected pyroglutamates with strong bases lead to a Boc migration from the N-atom to the C2 position when no or poor electrophiles are being used.

Selenolysine: A New Tool for Traceless Isopeptide Bond Formation

Despite their biological importance, post-translationally modified proteins are notoriously difficult to produce in a homogeneous fashion by using conventional expression systems. Chemical protein synthesis or semisynthesis offers a solution to this problem; however, traditional strategies often rely on sulfur-based chemistry that is incompatible with the presence of any cysteine residues in the target protein. To overcome these limitations, we present the design and synthesis of γ-selenolysine, a selenol-containing form of the commonly modified proteinogenic amino acid, lysine. The utility of γ-selenolysine is demonstrated with the traceless ligation of the small ubiquitin-like modifier protein, SUMO-1, to a peptide segment of human glucokinase. The resulting polypeptide is poised for native chemical ligation and chemoselective deselenization in the presence of unprotected cysteine residues. Selenolysine's straightforward synthesis and incorporation into synthetic peptides marks it as a universal handle for conjugating any ubiquitin-like modifying protein to its target.

Zelkovamycin is an OXPHOS Inhibitory Member of the Argyrin Natural Product Family

Natural products (NPs) are an important inspirational source for developing drugs and chemical probes. In 1999, the group of ōmura reported the constitutional elucidation of zelkovamycin. Although largely unrecognized so far, this NP displays structural s