28334-73-8

Basic information

• Product Name: (S)-2-(2-((tert-Butoxycarbonyl)aMino)acetaMido)-3-Methylbutanoic acid
• Synonyms: (S)-2-(2-((tert-Butoxycarbonyl)aMino)acetaMido)-3-Methylbutanoic acid
• CAS NO: 28334-73-8
• Molecular Formula: C₁₂H₂₂N₂O₅
• Molecular Weight: 274.31348
• Mol File: 28334-73-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 109-113°C
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (S)-2-(2-((tert-Butoxycarbonyl)aMino)acetaMido)-3-Methylbutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(2-((tert-Butoxycarbonyl)aMino)acetaMido)-3-Methylbutanoic acid(28334-73-8)
• EPA Substance Registry System: (S)-2-(2-((tert-Butoxycarbonyl)aMino)acetaMido)-3-Methylbutanoic acid(28334-73-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 28334-73-8(Hazardous Substances Data)

Usage

General Description

(S)-2-(2-((tert-Butoxycarbonyl)amino)acetamido)-3-methylbutanoic acid, also known as Boc-L-lysine, is a chemical compound with the molecular formula C13H24N2O5. It is an amino acid derivative, commonly used in peptide synthesis as a protecting group for the amino group of lysine. The Boc group is a protecting group used to block the reactive amine group in order to prevent unwanted reactions during peptide synthesis. (S)-2-(2-((tert-Butoxycarbonyl)aMino)acetaMido)-3-Methylbutanoic acid is a white to off-white solid and is soluble in organic solvents. It is utilized in the pharmaceutical and biotechnology industries for the production of pharmaceuticals, peptides, and research chemicals.

Upstream product

• 1963-21-9 L-glycyl-L-valine 
• 74651-77-7 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4070-48-8 L-Valine methyl ester 
• 16652-76-9 L-valine benzyl ester p-toluenesulfonate salt 
• 4530-20-5 BOC-glycine 
• 58871-93-5 (S)-methyl 2-(2-((tert-butoxycarbonyl)amino)acetamido)-3-methylbutanoate 
• 66415-00-7 N-t-butoxycarbonylglycyl-L-valine benzyl ester 

Downstream Products

• 147864-51-5 Boc-Gly-Val-Sar-OCH₂Ph 
• 158342-61-1 <3(S),4(S)>-2,4,5-trideoxy-4-<<2-<<<<(1,1-dimethylethoxy)carbonyl>amino>acetyl>amino>-3-methyl-1-oxobutyl>amino>-2,2-difluoro-5-<4-(2-methoxy-2-oxoethoxy)phenyl>-N-(phenylmethyl)-L-glycero-pentonamide 
• 158342-62-2 <3(S),4(S)>-2,4,5-trideoxy-4-<<2-<<<<(1,1-dimethylethoxy)carbonyl>amino>acetyl>amino>-3-methyl-1-oxobutyl>amino>-2,2-difluoro-5-<4-<2-oxo-2-(pentafluorophenoxy)ethoxy>phenyl>-N-(phenylmethyl)-L-glycero-pentonamide 
• 158342-63-3 <9(S),12(S)>-α,α-difluoro-β-hydroxy-9-(1-methylethyl)-4,7,10-trioxo-N-(phenylmethyl)-2-oxa-5,8,11-triazabicyclo<12,2,2>octadeca-14,16,17-triene-12-propanamide 
• 1412893-40-3 C₄₈H₇₃N₅O₉ 
• 1202022-06-7 (28R,29R)-arenamide A 
• 1412911-49-9 C₃₆H₅₇N₅O₇ 
• 1412911-50-2 C₃₆H₅₇N₅O₇ 
• 1412893-35-6 C₃₆H₅₉N₅O₈ 
• 1412893-36-7 C₃₆H₅₉N₅O₈ 
• 1412893-37-8 C₃₆H₅₉N₅O₈ 
• 1412893-38-9 C₄₈H₇₃N₅O₉ 
• 1412893-39-0 C₄₈H₇₃N₅O₉ 
• 1493792-61-2 tert-butoxycarbonyl-Gly-Val-4-pyrrolylanilide 

Relevant articles and documents

A clickable, highly soluble oligopeptide that easily forms organogels

An artificial peptide, N3-GVGV-OMe (G, glycine; V, valine), which mimics the repeating GAGA (A, alanine) sequence in Bombix Mori silk, was synthesised via solution-phase synthesis. Compared with N3-GAGA-OMe sequence, N3-GVGV-OMe showed high solubility in common organic solvents (such as CHCl3, THF and CH2Cl2), and easily formed organogels simply by adding poor solvents (such as toluene or ether) to the peptide solution at room temperature. The hierarchical nanostructure of N3-GVGV-OMe organogel was dependent on the nature of the poor solvents, although in all cases, β-sheets were formed exclusively. Gels formed in ether showed higher level hierarchical assembly, as evidenced by AFM and CD studies. Solution-state FT-IR analysis showed that the pre-organisation of the peptides in solution was not significant, and well-defined antiparallel β-sheets were formed after the addition of the poor solvent. The high solubility and strong tendency for self-assembly of N3-GVGV-OMe, together with its terminal azide group, might facilitate the modification of functional organic molecules even macromolecules for better nanostructure control.

CASPASE PROBES FOR DETECTION OF APOPTOSIS

The present disclosure relates to glycine-containing probes that are capable of binding to active caspases and can be used for detecting apoptosis. In particular, the probes can be used to determine the degree or incidence of caspase-mediated apoptosis and conditions associated therewith. In one embodiment, the probes are cell permeable and function intracellularly. The disclosure includes a caspase probe having the formula: R1-X-R2 wherein R1 is absent, a detectable or non-detectable N-terminal group, or a chelator; X is a group that recognizes a caspase; and R2 is a reactive group that binds to a caspase. The caspase probes can be used for purposes of diagnostic testing, research, and drug development, among other uses. The present disclosure further relates to compositions comprising at least one probe and an excipient, as well as kits comprising at least one probe and instructions for use.

Guanidine hydrochloride as an organocatalyst for N-Boc protection of amino groups

A simple and efficient method for the chemoselective N-Boc protection of the amine moiety in a variety of compounds is described using di-tert-butyl dicarbonate and guanidine hydrochloride as an organocatalyst in ethanol at 35-40°C. Selective mono-N-Boc protection of diamines and chemoselective protection of hydroxylamines without formation of any side products is achieved. Amino acids and peptides are N-Boc protected efficiently in excellent yields under convenient reaction conditions.