CAS 252049-18-6

N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-S-(phenylmethyl)-D-cysteine

Description:

N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-S-(phenylmethyl)-D-cysteine, commonly referred to as Fmoc-D-Cys(Ph-CH2)-OH, is a derivative of cysteine, an amino acid known for its thiol group. This compound features a protective Fmoc (fluorenylmethyloxycarbonyl) group, which is commonly used in peptide synthesis to protect the amino group during the coupling process. The presence of the phenylmethyl group (benzyl group) attached to the sulfur atom of the cysteine enhances its hydrophobic character and can influence the compound's solubility and reactivity. The structure allows for potential applications in peptide synthesis, particularly in the development of peptides with specific functionalities or in drug design. The compound is typically solid at room temperature and may exhibit stability under standard laboratory conditions, although it should be handled with care due to the reactive thiol group. Its unique structural features make it a valuable building block in the field of medicinal chemistry and biochemistry.

Formula: C₂₅H₂₃NO₄S

InChI: InChI=1S/C25H23NO4S/c27-24(28)23(16-31-15-17-8-2-1-3-9-17)26-25(29)30-14-22-20-12-6-4-10-18(20)19-11-5-7-13-21(19)22/h1-13,22-23H,14-16H2,(H,26,29)(H,27,28)/t23-/m1/s1

InChI key: InChIKey=AKXYVGAAQGLAMD-HSZRJFAPSA-N

SMILES: C(OC(N[C@H](CSCC1=CC=CC=C1)C(O)=O)=O)C2C=3C(C=4C2=CC=CC4)=CC=CC3

Synonyms:

• (2S)-3-Benzylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• D-Cysteine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-S-(phenylmethyl)-
• N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-S-(phenylmethyl)-D-cysteine

D-Cysteine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-S-(phenylmethyl)-

CAS: 252049-18-6

Formula: C₂₅H₂₃NO₄S

Purity: 98%

Color and Shape: Solid

Molecular weight: 433.5194

Ref: IN-DA002QWW

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-S-benzyl-d-cysteine

CAS: 252049-18-6

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-S-benzyl-d-cysteine

Purity: 98%

Molecular weight: 433.52g/mol

Ref: 54-OR1001389

D-Cysteine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-S-(phenylmethyl)-

CAS: 252049-18-6

Purity: 98%

Molecular weight: 433.519989

Ref: 10-F862262

Fmoc-D-Cys(Bzl)-OH

CAS: 252049-18-6

The compound Fmoc-D-Cys(Bzl)-OH is a chiral homologue of the protonated amino acid D-Cys. The configuration of the proton in this molecule has been determined by proton nmr experiments. This compound is synthesized from the racemic mixture by reductive amination and deprotonation with sodium borohydride. The reagents are an organophosphate and an ester, which react in order to form a new carbon-carbon bond. The postulated enantiomers are screened for their activity against phospholipase A2, which cleaves ester bonds on phospholipids. One enantiomer has been shown to have more potent activity than its counterpart, suggesting that it is the desired product.

Formula: C₂₅H₂₃NO₄S

Purity: Min. 95%

Molecular weight: 433.52 g/mol

Ref: 3D-FF111332