Mmaf

Base Information

• Chemical Name: Mmaf
• CAS No.: 745017-94-1
• Molecular Formula: C39H65N5O8
• Molecular Weight: 731.974
• UNII: 1Z1AI9IW5L
• DSSTox Substance ID: DTXSID601031563
• Nikkaji Number: J2.310.331A
• Wikipedia: Monomethyl_auristatin_F
• Wikidata: Q76415591
• ChEMBL ID: CHEMBL3359822
• Mol file: 745017-94-1.mol

Synonyms:MMAF peptide;monomethyl auristatin F;monomethylauristatin F

Chemical Property of Mmaf

Chemical Property:

• Boiling Point: 896.8±65.0 °C(Predicted)
• PKA: 3.56±0.10(Predicted)
• PSA: 166.61000
• Density: 1.116±0.06 g/cm3(Predicted)
• LogP: 4.21420
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in DMSO
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 21
• Exact Mass: 731.48331405
• Heavy Atom Count: 52
• Complexity: 1160

Purity/Quality:

MonomethylAuristatinF ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(CC(=O)N1CCCC1C(C(C)C(=O)NC(CC2=CC=CC=C2)C(=O)O)OC)OC)N(C)C(=O)C(C(C)C)NC(=O)C(C(C)C)NC
• Isomeric SMILES: CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@@H]([C@@H](C)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O)OC)OC)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC
• Description: MMAF (Monomethylauristatin F) is an effective tubulin polymerization inhibitor, used as an anti-tumor drug. MMAF (Monomethylauristatin F) is widely used as the cytotoxic component of antibody-conjugated drugs (ADCs), such as Vorsetuzumab mafodotin and SGN-CD19A.

Technology Process of Mmaf

There total 40 articles about Mmaf 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: 5.0%

(S)-methyl 2-((2R,3R)-3-((S)-1-((6S,9S,12S,13R)-12-((S)-sec-butyl)-6,9-diisopropyl-13-methoxy-2,2,5,11-tetramethyl-4,7,10-trioxo-3-oxa-5,8,11-triazapentadecan-15-oyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoate (1415246-61-5) → (S)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-N,3-dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamido)-3-methoxy-5-methylheptanoyl)-pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoic acid (745017-94-1)

Guidance literature:

(S)-methyl 2-((2R,3R)-3-((S)-1-((6S,9S,12S,13R)-12-((S)-sec-butyl)-6,9-diisopropyl-13-methoxy-2,2,5,11-tetramethyl-4,7,10-trioxo-3-oxa-5,8,11-triazapentadecan-15-oyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoate; With hydrogenchloride; In 1,4-dioxane; toluene; at 20 ℃; for 16h;

With hydrogenchloride; acetic acid; In water; at 20 ℃; for 24h;

Reference yield:

(S)-methyl 2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-N,3-dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamido)-3-methoxy-5-methyl-heptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoate → (S)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-N,3-dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamido)-3-methoxy-5-methylheptanoyl)-pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoic acid (745017-94-1)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; at 20 ℃; for 0.583333h;

Reference yield:

(S)-methyl 2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((tert-butoxycarbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)-pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoate (1415246-55-7) → (S)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-N,3-dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamido)-3-methoxy-5-methylheptanoyl)-pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoic acid (745017-94-1)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C

2: 4-methyl-morpholine; HATU / N,N-dimethyl-formamide / 4 h / 20 °C

3: water; lithium hydroxide / methanol / 2 h / 20 °C

4: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; water; HATU; lithium hydroxide; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

upstream raw materials:

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

(2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((tert-butoxycarbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoic acid

(S)-methyl 2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((tert-butoxycarbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)-pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoate

C₃₄H₅₆N₄O₇*ClH

Downstream raw materials:

((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((S)-2-(dimethylamino)-3-methylbutyrylamino)-N,3-dimethylbutyrylamino)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropionyl)-L-phenylalanine

C₂HF₃O₂*C₅₅H₉₆N₆O₁₃

C₅₁H₈₈N₆O₁₃*ClH

C₅₂H₇₉N₇O₁₁

Refernces

• 1、 -. "NOVEL CONNECTED BODY AND USE THEREOF IN SPECIFIC CONJUGATION BETWEEN BIOMOLECULE AND DRUG". . . Retrieved 2021/05/14.
• 2、 -. "CONJUGATION OF A CYTOTOXIC DRUG WITH BIS-LINKAGE". . . Retrieved 2020/01/08.