28862-80-8

Basic information

• Product Name: Z-D-MET-OH
• Synonyms: N-CBZ-D-METHIONINE;N-CARBOBENZOXY-D-METHIONINE;N-ALPHA-CBZ-D-METHIONINE;N-ALPHA-CARBOBENZOXY-D-METHIONINE;N-ALPHA-BENZYLOXYCARBONYL-D-METHIONINE;Z-D-MET-OH;Z-D-METHIONINE;CBZ-D-MET-OH
• CAS NO: 28862-80-8
• Molecular Formula: C₁₃H₁₇NO₄S
• Molecular Weight: 283.34
• Product Categories: Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids
• Mol File: 28862-80-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 67-69°C
• Boiling Point: 504.7 °C at 760 mmHg
• Flash Point: 259 °C
• Appearance: /Solid
• Density: 1.253
• Vapor Pressure: 5.22E-11mmHg at 25°C
• Refractive Index: 26 ° (C=1, MeOH)
• Storage Temp.: Store at RT.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Z-D-MET-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-D-MET-OH(28862-80-8)
• EPA Substance Registry System: Z-D-MET-OH(28862-80-8)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 28862-80-8(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

N-Cbz-D-methionine is an N-Cbz-protected form of D-Methionine (M260550). D-Methionine is an isomer of L-Methionine (M260440), and is known to be a cytoprotectant against Cisplatin (C499500), an anticancer agent. D-Methionine is also used to prevent noise- and drug-induced hearing loss, as well as hair loss (all of which may also be caused by Cisplatin or aminoglycosides).

InChI:InChI=1/C13H17NO4S/c1-19-8-7-11(12(15)16)14-13(17)18-9-10-5-3-2-4-6-10/h2-6,11H,7-9H2,1H3,(H,14,17)(H,15,16)/t11-/m1/s1

Upstream product

• 348-67-4 D-methionine 
• 501-53-1 benzyl chloroformate 
• 59-51-8 DL-methionine 
• 127862-75-3 2-Benzyloxycarbonylamino-4-methylsulfanyl-butyric acid 2,2,2-trifluoro-ethyl ester 
• 921-01-7 rac-cysteine 
• 4434-61-1 N-(benzyloxycarbonyl)methionine 
• 62-53-3 aniline 
• 64-17-5 ethanol 

Downstream Products

• 1456813-89-0 C₂₁H₂₆N₂O₄S 
• 172485-84-6 Cbz-D-Met-NH₂ 
• 1370617-83-6 Cbz-(L)Met-NHFurfuryl 
• 1053631-21-2 [(1R,2S,3S,4R)-4-Benzyloxycarbonylamino-6-methylsulfanyl-1-(2-methylsulfanyl-ethyl)-2,3-bis-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-carbamic acid benzyl ester 
• 1054654-15-7 (4R,5S,6S,7R)-1,3-Dibenzyl-4,7-bis-(2-methylsulfanyl-ethyl)-5,6-bis-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]diazepan-2-one 
• 1026909-70-5 [(R)-1-(Methoxy-methyl-carbamoyl)-3-methylsulfanyl-propyl]-carbamic acid benzyl ester 
• 245107-60-2 (2R,4R)-2-tert-Butyl-4-(2-methyl-allyl)-4-(2-methylsulfanyl-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 214677-47-1 (3R)-3-benzyloxycarbonylamino-1-tert-butoxycarbonylaminopyrrolidin-2-one 
• 245107-61-3 (R)-2-Benzyloxycarbonylamino-4-methyl-2-(2-methylsulfanyl-ethyl)-pent-4-enoic acid 
• 793653-83-5 3(R)-benzyloxycarbonylamino-1-aminopyrrolidin-2-one 

Relevant articles and documents

Enantioselective inclusion of pyrene-1-sulfonate salts of α-amino acids with crystals of α-cyclodextrin

Enantioselective inclusion of α-amino acids with crystals of α-cyclodextrin (α-CD) has been achieved by converting the amino acids into sulfonate salts with pyrene-1-sulfonic acid (PyS). For example, crystals of α-CD selectively include L-leucine/PyS (1:1) salt in a host/guest ratio of ～1 with 92%ee from a solution of the racemic salt in ethanol/N-methylformamide (91:9) at 40 °C. Under conditions optimized for individual amino acids, the PyS salts of valine, phenylalanine, and methionine are also included with good enantioselectivities (up to 86%ee). Mechanistic studies for the inclusion of leucine/PyS salt reveals that the enantioselectivity originates from the difference in stability between the inclusion complexes of D- and L-leucine/PyS salts with α-CD in crystals.

POLYCYCLIC TLR7/8 ANTAGONISTS AND USE THEREOF IN THE TREATMENT OF IMMUNE DISORDERS

The present invention relates to compounds of Formula (I) and pharmaceutically acceptable compositions thereof, useful as toll-like receptor 7/8 (TLR7/8) antagonists. In Formula (I), Ring A is aryl or heteroaryl; Ring B is aryl or heteroary; and X is C(R4)2, O, NR4, S, S(R4), or S(R4)2.

Insecticidal Properties of Some Derivatives of L-Canavanine

The canavanine derivatives D-canavanine and L-homocanavanine as well as the 1-methyl and 1-ethyl esters of L-canavanine were synthesized and evaluated for biological activity in fifth instar larvae of the tobacco hornworm, Manduca sexta .While L-homocanavanine did not increase intrinsic toxicity, it was as deleterious as L-canavanine.D-Canavanine was biologically active, as demonstrated by its ability to cause larval edema, but the D-enantiomer had little ability to elicit the larval growth inhibition and pupal deformity which are hallmarks of canavanine toxicosis and was postulated to be linked to aberrant protein production.The 1-methyl and 1-ethyl esters of L-canavanine were synthesized to determine if enhancing canavanine's hydrophobicity might increase its bioavailability.Our experiments revealed that these esters are less toxic than canavanine; the ethyl ester disrupted larval growth more than did the methyl analogue. - Keywords: L-Canavanine; D-canavanine; L-homocanavanine; 1-methyl-L-canavanine; 1-ethyl-L-canavanine; Manduca sexta