CAS 71989-29-2

N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-methionine 4-nitrophenyl ester

Description:

N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-methionine 4-nitrophenyl ester, commonly referred to as Fmoc-L-methionine-4-nitrophenyl ester, is a chemical compound used primarily in peptide synthesis as a protecting group for the amino acid methionine. This compound features a fluorenylmethoxycarbonyl (Fmoc) group, which is a widely utilized protective group in solid-phase peptide synthesis due to its stability under basic conditions and ease of removal under mild acidic conditions. The presence of the 4-nitrophenyl ester moiety enhances the reactivity of the carboxylic acid, facilitating coupling reactions with amines during peptide formation. The compound is typically a white to off-white solid and is soluble in organic solvents like dimethylformamide (DMF) and dichloromethane (DCM). Its molecular structure allows for selective reactions, making it valuable in the synthesis of peptides and other complex organic molecules. Safety precautions should be taken when handling this compound, as with many chemical reagents, due to potential toxicity and reactivity.

Formula: C₂₆H₂₄N₂O₆S

InChI: InChI=1S/C26H24N2O6S/c1-35-15-14-24(25(29)34-18-12-10-17(11-13-18)28(31)32)27-26(30)33-16-23-21-8-4-2-6-19(21)20-7-3-5-9-22(20)23/h2-13,23-24H,14-16H2,1H3,(H,27,30)/t24-/m0/s1

InChI key: InChIKey=UAAQHWWCPKRGKF-DEOSSOPVSA-N

SMILES: C(OC(N[C@H](C(OC1=CC=C(N(=O)=O)C=C1)=O)CCSC)=O)C2C=3C(C=4C2=CC=CC4)=CC=CC3

Synonyms:

• L-Methionine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 4-nitrophenyl ester
• N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-methionine 4-nitrophenyl ester
• (S)-4-Nitrophenyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(methylthio)butanoate