106719-44-2

Basic information

• Product Name: BOC-D-LYS-OH
• Synonyms: BOC-D-LYSINE;BOC-D-LYS-OH;N-ALPHA-T-BUTOXYCARBONYL-D-LYSINE;N-ALPHA-T-BUTYLOXYCARBONYL-D-LYSINE;N-ALPHA-TERT-BUTYLOXYCARBONYL-D-LYSINE;N-α-Boc-D-lysine;NALPHA-tert-Butoxycarbonyl-D-lysine;N-.ALPHA.-BOC-D-LYSINE
• CAS NO: 106719-44-2
• Molecular Formula: C₁₁H₂₂N₂O₄
• Molecular Weight: 246.3
• EINECS: 237-303-4
• Product Categories: Lysine [Lys, K];Boc-Amino Acids and Derivative;Amino Acids;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
• Mol File: 106719-44-2.mol

Chemical Properties

• Melting Point: 198 °C
• Boiling Point: 410.5 °C at 760 mmHg
• Flash Point: 202 °C
• Appearance: /
• Density: 1.113 g/cm³
• Vapor Pressure: 6.91E-08mmHg at 25°C
• Refractive Index: -22 ° (C=2, MeOH)
• Storage Temp.: 2-8°C
• PKA: 3.92±0.21(Predicted)
• CAS DataBase Reference: BOC-D-LYS-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-LYS-OH(106719-44-2)
• EPA Substance Registry System: BOC-D-LYS-OH(106719-44-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 4-7-28-35-44
• WGK Germany: 3
• Hazardous Substances Data: 106719-44-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BOC-D-LYS-OH is used as a building block for the synthesis of various pharmaceutical compounds due to its unique properties as an N-Boc-protected form of D-Lysine. Its ability to reduce non-enzymatic glycation makes it a valuable component in the development of drugs targeting glycation-related diseases.
Used in Drug Delivery Systems:
BOC-D-LYS-OH is used as a polymeric drug carrier for the development of targeted drug delivery systems. Its nonspecific adhesion-promoting properties as part of poly-D-lysine polypeptide chains allow for the creation of drug carriers that can enhance the delivery and efficacy of therapeutic agents.
Used in Research and Development:
BOC-D-LYS-OH is used as a research compound for studying the properties and potential applications of D-Lysine and its derivatives. Its unique chemical structure and properties make it an important tool in the development of new drugs and therapies.
Used in Chemical Synthesis:
BOC-D-LYS-OH is used as an intermediate in the chemical synthesis of various compounds, particularly those related to the pharmaceutical and biotechnology industries. Its versatility as a protected form of D-Lysine allows for the creation of a wide range of products with diverse applications.

InChI:InChI=1/C11H22N2O4/c1-11(2,3)17-10(16)13-8(9(14)15)6-4-5-7-12/h8H,4-7,12H2,1-3H3,(H,13,16)(H,14,15)/t8-/m1/s1

Upstream product

• 106326-22-1 BOC-Lys(Z)-NH₂ 
• 7274-88-6 D-lysine hydrochloride 
• 34404-32-5 (R)-2-amino-6-(((benzyloxy)carbonyl)amino)hexanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 55878-47-2 (R)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoic acid 

Downstream Products

• 122546-52-5 N^α-tert-butyloxycarbonyl-N^ε-nicotinoyl-D-lysine 
• 166898-11-9 2-(R)-<<(tert-butyloxy)carbonyl>amino>-6-(3-o-tolylureido)hexanoic acid 
• 106691-72-9 3(R)--2-oxoperhydroazepine 
• 115186-31-7 (2R)-2-(tert-butoxycarbonylamino)-6-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid 
• 1008161-75-8 N-methyl-((R)-azepan-2-one-3-ylamino-(R)-oxo-3-phenylpropan-2-yl)dec-9-enamide 
• 1067658-76-7 N-methyl-((R)-azepan-2-one-3-ylamino-(S)-oxo-3-phenylpropan-2-yl)dec-9-enamide 
• 1067659-02-2 tert-butyl methyl((R)-azepan-2-one-3-ylamino-(R)-oxo-3-phenylpropan-2-yl)carbamate 
• 1067658-96-1 tert-butyl methyl((R)-azepan-2-one-3-ylamino-(S)-oxo-3-phenylpropan-2-yl)carbamate 
• 55878-47-2 (R)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoic acid 
• 55757-60-3 methyl (2R)-6-amino-2-{[(tert-butoxy)carbonyl]amino}hexanoate 

Relevant articles and documents

Reconstitution of peptidoglycan cross-linking leads to improved fluorescent probes of cell wall synthesis

The peptidoglycan precursor, Lipid II, produced in the model Gram-positive bacterium Bacillus subtilis differs from Lipid II found in Gram-negative bacteria such as Escherichia coli by a single amidation on the peptide side chain. How this difference affects the cross-linking activity of penicillin-binding proteins (PBPs) that assemble peptidoglycan in cells has not been investigated because B. subtilis Lipid II was not previously available. Here we report the synthesis of B. subtilis Lipid II and its use by purified B. subtilis PBP1 and E. coli PBP1A. While enzymes from both organisms assembled B. subtilis Lipid II into glycan strands, only the B. subtilis enzyme cross-linked the strands. Furthermore, B. subtilis PBP1 catalyzed the exchange of both d-amino acids and d-amino carboxamides into nascent peptidoglycan, but the E. coli enzyme only exchanged d-amino acids. We exploited these observations to design a fluorescent d-amino carboxamide probe to label B. subtilis PG in vivo and found that this probe labels the cell wall dramatically better than existing reagents.

Synthesis of Unnatural Amino Acids

This communication presents efficient synthetic procedures for the D and L isomers of Nα-tert-butyloxycarbonyl-Nε-benzyloxycarbonyl-Nε-isopropyllysine dicyclohexylamine salt (Nα-Boc-Nε-Z-Ilys DCHA salt), the D and L isomers of Nα-tert-butyloxycarbonyl-Nεnicotinoyllysine (Nα-Boc-Niclys), β-(3-quinolyl)-D,L-alanine (3-Quinal), and the resolution into the D and L isomers of 3-Quinal.

Synthetic peptides having pituitary growth hormone releasing activity

Novel pentapeptides having the following amino acid sequenceX--Y--Z--E--G--J--Lwherein X is selected from a group consisting of --NH 2, --NHCH 3, and --N(CH 3) 2 ; Y is selected from a group consisting of D-lysine and D-arginine; Z and J are independently selected from a group consisting of tyrosine, tryptophan, and phenylalanine; E and G are independently selected from a group consisting of D-tyrosine, D-tryptophan, and D-phenylalanine; and L is a C-terminal functional group selected from a group consisting of amide, amide lower alkyl, amide di(lower alkyl), lower alkoxy, hydroxy, and carboxy and the lower ester derivatives thereof; and the pharmaceutically acceptable salts thereof. These peptides act directly on the pituitary to release growth hormone therefrom.