203866-19-7 Usage
Description
(2S,4S)-FMOC-4-FLUORO-PYRROLIDINE-2-CARBOXYLIC ACID, also known as Fmoc-cis-4-fluoro-Pro-OH, is a synthetic compound characterized by its white powder form. It is a chiral molecule with specific stereochemistry, featuring a 4-fluoro substituent on a pyrrolidine ring and a carboxylic acid group. (2S,4S)-FMOC-4-FLUORO-PYRROLIDINE-2-CARBOXYLIC ACID is protected with a 9-fluorenylmethoxycarbonyl (Fmoc) group, which is commonly used in peptide synthesis to protect the amino group of amino acids.
Uses
Used in Pharmaceutical Industry:
(2S,4S)-FMOC-4-FLUORO-PYRROLIDINE-2-CARBOXYLIC ACID is used as a key intermediate in the synthesis of peptides containing substituted proline residues. The incorporation of this compound into peptide sequences can modulate the conformation and biological activity of the resulting peptides, making it valuable for the development of novel therapeutic agents.
Used in Peptide Synthesis:
In the field of organic chemistry and peptide synthesis, (2S,4S)-FMOC-4-FLUORO-PYRROLIDINE-2-CARBOXYLIC ACID serves as a protected amino acid building block. Its Fmoc protection allows for selective deprotection and coupling reactions during the assembly of complex peptide structures, facilitating the synthesis of biologically active peptides with specific pharmacological properties.
Used in Research and Development:
(2S,4S)-FMOC-4-FLUORO-PYRROLIDINE-2-CARBOXYLIC ACID is utilized in academic and industrial research settings for the exploration of new peptide-based drugs, the study of protein folding and stability, and the development of new methods in peptide chemistry. Its unique structural features and reactivity make it a valuable tool for advancing scientific knowledge and innovation in these areas.
Check Digit Verification of cas no
The CAS Registry Mumber 203866-19-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,0,3,8,6 and 6 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 203866-19:
(8*2)+(7*0)+(6*3)+(5*8)+(4*6)+(3*6)+(2*1)+(1*9)=127
127 % 10 = 7
So 203866-19-7 is a valid CAS Registry Number.
203866-19-7Relevant articles and documents
Evidence for a stereoelectronic effect in human oxygen sensing
Loenarz, Christoph,Mecinovic, Jasmin,Chowdhury, Rasheduzzaman,McNeill, Luke A.,Flashman, Emily,Schofield, Christopher J.
supporting information; experimental part, p. 1784 - 1787 (2009/09/07)
How PHDs achieve specificity: trans-4-prolyl hydroxylation of the transcription factor HIF occurs with stereochemical retention. Substrate-analogue studies show how the von Hippel Lindau tumor suppressor protein (pVHL) and the oxygen-sensing hydroxylases (PHDs) achieve specificity for hydroxy prolyl/prolyl residues for the C4-exo/endo prolyl conformations, respectively.
Practical synthesis of Boc and Fmoc protected 4-fluoro and 4-difluoroprolines from trans-4-hydroxyproline
Demange, Luc,Menez, Andre,Dugave, Christophe
, p. 1169 - 1172 (2007/10/03)
Boc-cis-4-fluoro-L-proline and 4-difluoro-L-proline, usable in classical peptide synthesis, were obtained in respectively 71% (3 steps) and 65% (4 steps) overall yields from the readily available trans-4-hydroxy-L-proline methyl ester. The corresponding fluorinated trans-isomer was isolated in 24% yield (5 steps). Transformation of Boc-protected compounds to their Fmoc-equivalents was performed in high yields.
