Fmoc-D-Met-OH

Base Information

• Chemical Name: Fmoc-D-Met-OH
• CAS No.: 112883-40-6
• Molecular Formula: C₂₀H₂₁NO₄S
• Molecular Weight: 371.457
• Hs Code.: 29309090
• DSSTox Substance ID: DTXSID90426316
• Nikkaji Number: J1.446.562F
• Wikidata: Q72478568
• Mol file: 112883-40-6.mol

Synonyms:Fmoc-D-Met-OH;112883-40-6;Fmoc-D-methionine;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanylbutanoic acid;112833-40-6;(((9H-Fluoren-9-yl)methoxy)carbonyl)-D-methionine;D-Methionine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;N-Fmoc-D-methionine;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-methionine;MFCD00062958;Fmoc-D-Met-OH, 98%;SCHEMBL800305;2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanyl-butyric acid;DTXSID90426316;BUBGAUHBELNDEW-GOSISDBHSA-N;AKOS015852501;AM81981;CS-W009765;HY-W009049;AC-17108;DS-14999;PD196650;F0594;F10554;M03369;EN300-1556130;A847881;J-300197;Q-101594;N-(9H-Fluorene-9-ylmethoxycarbonyl)-S-methyl-D-homocysteine;N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-methionine (Fmoc-D-Met-OH);(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanyl-butyric acid;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-(methylsulfanyl)butanoic acid;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(methylthio)butanoic acid

Chemical Property of Fmoc-D-Met-OH

Chemical Property:

• Vapor Pressure: 5.8E-16mmHg at 25°C
• Melting Point: 132 °C
• Refractive Index: 30 ° (C=1, DMF)
• Boiling Point: 614.6 °C at 760 mmHg
• PKA: 3.72±0.10(Predicted)
• Flash Point: 325.5 °C
• PSA: 100.93000
• Density: 1.282 g/cm³
• LogP: 4.12230
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMF (Slightly), Methanol (Slightly)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 371.11912932
• Heavy Atom Count: 26
• Complexity: 478

Purity/Quality:

99% ^*data from raw suppliers

N-Fmoc-D-methionine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CSCC[C@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: N-Fmoc-D-methionine is an N-Fmoc-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).

Technology Process of Fmoc-D-Met-OH

There total 3 articles about Fmoc-D-Met-OH which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-Fmoc-methionine (144701-23-5) → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + Nα-fluorenyl-9-methoxycarbonyl-D-Met (71989-28-1,144701-23-5,112883-40-6)

Guidance literature:

With trifluoroacetic acid; In hexane; isopropyl alcohol; at 25 ℃; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/bkcs.11694

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + Nα-fluorenyl-9-methoxycarbonyl-D-Met (71989-28-1,144701-23-5,112883-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium carbonate / water; 1,4-dioxane / Cooling with ice

1.2: 5 h / 20 °C

2.1: trifluoroacetic acid / isopropyl alcohol; hexane / 25 °C / Resolution of racemate

With sodium carbonate; trifluoroacetic acid; In 1,4-dioxane; hexane; water; isopropyl alcohol;

DOI:10.1002/bkcs.11694

Reference yield:

DL-methionine (59-51-8,26062-47-5,58576-49-1) → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + Nα-fluorenyl-9-methoxycarbonyl-D-Met (71989-28-1,144701-23-5,112883-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium carbonate / water; 1,4-dioxane / Cooling with ice

1.2: 5 h / 20 °C

2.1: trifluoroacetic acid / isopropyl alcohol; hexane / 25 °C / Resolution of racemate

With sodium carbonate; trifluoroacetic acid; In 1,4-dioxane; hexane; water; isopropyl alcohol;

DOI:10.1002/bkcs.11694

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

N-Fmoc-methionine

DL-methionine

Downstream raw materials:

L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-L-proline amide

H-Tyr-D-Met-Gly-Phe-Hyp(Man)-NH₂

Refernces

• 1、 Islam, Md. Fokhrul,Adhikari, Suraj,Paik, Man-Jeong,Lee, Wonjae. "Determination of Chemical and Enantiomeric Purity of α-Amino Acids and their Methyl Esters as N-Fluorenylmethoxycarbonyl Derivatives Using Amylose-derived Chiral Stationary Phases". . p. 332 - 338. Retrieved 2019/04/13.