Boc-N-methyl-L-leucine

Synonym(s):Boc-N-methyl-L-leucine;Boc-N-Me-Leu-OH;N-α-t.-Boc-N-α-methyl-L-leucine

CAS NO.：53363-89-6
Empirical Formula: C12H23NO4
Molecular Weight: 245.32
MDL number: MFCD00038522
SAFETY DATA SHEET (SDS)
Update Date: 2024-07-02 08:55:06

What is Boc-N-methyl-L-leucine?

Description

Boc-N-methyl-L-leucine is the BOC (tert-butyloxycarbonyl) protected N-methylated leucine. The N-methylated amino acid is quite useful in the peptide synthesis, giving a lot of improved properties to peptide. Studies have shown that peptide containing N-methylated amino acids obtain increased proteolytic stability, increased membrane permeability, and altered conformation. The effects of N-methylated amino acids are quite important in the development of therapeutic peptide compound as well as in the assay of biological activity of some modified peptides. BOC group can be easily removed by treatment with strong acids such as trifluoroacetic acid.

The Uses of Boc-N-methyl-L-leucine

Boc-N-methyl-L-leucine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Biological Activity

Boc-N-methyl-L-leucine is a peptidyl nucleobase that has been shown to inhibit tumor cell growth and induce tumor regression in animal models. It is an amide of leucine and the antibiotic aminouracil, which is a guanine analogue. Boc-N-methyl-L-leucine has also shown to inhibit tumor growth by inhibiting mitochondrial membrane potential, which may lead to cell death in cancer cells. This compound has been shown to be effective against both solid tumors and leukemia cell lines. Boc-N-methyl-L-leucine also inhibits the proliferation of human prostate cancer cells by blocking the synthesis of nucleic acids and proteins.

References

https://en.wikipedia.org/wiki/Tert-Butyloxycarbonyl_protecting_group
http://pubs.acs.org/doi/abs/10.1021/cr030024z?src=recsys&journalCode=chreay

Properties of Boc-N-methyl-L-leucine

Melting point:	55-60 °C
Boiling point:	338.2±21.0 °C(Predicted)
Density	1.053±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,2-8°C
pka	4.04±0.21(Predicted)
form	Solid
color	White to off-white
optical activity	[α]20/D 36±2°, c = 1% in methylene chloride
BRN	2373250
InChI	InChI=1S/C12H23NO4/c1-8(2)7-9(10(14)15)13(6)11(16)17-12(3,4)5/h8-9H,7H2,1-6H3,(H,14,15)/t9-/m0/s1
CAS DataBase Reference	53363-89-6(CAS DataBase Reference)

Safety information for Boc-N-methyl-L-leucine

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.