86060-98-2

Basic information

• Product Name: FMOC-LYS(BOC)-OPFP
• Synonyms: FMOC-L-LYS(BOC)-OPFP;FMOC-LYSINE(BOC)-OPFP;FMOC-LYS(BOC)-OPFP;FMOC-N-EPSILON-BOC-L-LYSINE PENTAFLUOROPHENYL ESTER;NEPSILON-BOC-NALPHA-FMOC-L-LYSINE PENTAFLUOROPHENYL ESTER;N-ALPHA-FMOC-N-EPSILON-T-BUTYLOXYCARBONYL-L-LYSINE PENTAFLUOROPHENYL ESTER;N-ALPHA-FMOC-N-EPSILON-T-BOC-L-LYSINE PENTAFLUOROPHENYL ESTER;NALPHA-FMOC-NEPSILON-BOC-L-LYSINE PENTAFLUOROPHENYL ESTER
• CAS NO: 86060-98-2
• Molecular Formula: C₃₂H₃₁F₅N₂O₆
• Molecular Weight: 634.59
• EINECS: 276-256-4
• Product Categories: Amino Acids;Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series
• Mol File: 86060-98-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 135-145°C
• Boiling Point: 726.7 °C at 760 mmHg
• Flash Point: 393.3 °C
• Appearance: /
• Density: 1.324 g/cm³
• Vapor Pressure: 5.64E-21mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: −20°C
• PKA: 10.27±0.46(Predicted)
• CAS DataBase Reference: FMOC-LYS(BOC)-OPFP(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-LYS(BOC)-OPFP(86060-98-2)
• EPA Substance Registry System: FMOC-LYS(BOC)-OPFP(86060-98-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 86060-98-2(Hazardous Substances Data)

Usage

Description

FMOC-LYS(BOC)-OPFP, with the chemical name 9H-Fluoren-9-ylmethoxycarbonyl-L-lysine(2,2,2-trifluoroethyl) ester, is a synthetic lysine derivative. It is characterized by the presence of a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group, a trifluoroethyl (OPfp) ester, and a Boc-protected amino group. FMOC-LYS(BOC)-OPFP is a key building block in the synthesis of peptides and proteins, particularly in the preparation of motilin-like peptides.

Uses

Used in Pharmaceutical Industry:
FMOC-LYS(BOC)-OPFP is used as a synthetic building block for the preparation of motilin-like peptides, which are known for their gastrointestinal motility-stimulating activity. These peptides have potential therapeutic applications in treating gastrointestinal disorders and improving gut motility.
Used in Peptide Synthesis:
FMOC-LYS(BOC)-OPFP is used as a protected amino acid in solid-phase peptide synthesis (SPPS). The Fmoc protecting group allows for selective deprotection and coupling of amino acids during the synthesis process, while the Boc-protected amino group prevents side reactions. The trifluoroethyl ester (OPfp) provides a stable and easily removable protecting group for the carboxyl group, facilitating the synthesis of peptides with desired sequences and functionalities.

InChI:InChI=1/C32H31F5N2O6/c1-32(2,3)45-30(41)38-15-9-8-14-22(29(40)44-28-26(36)24(34)23(33)25(35)27(28)37)39-31(42)43-16-21-19-12-6-4-10-17(19)18-11-5-7-13-20(18)21/h4-7,10-13,21-22H,8-9,14-16H2,1-3H3,(H,38,41)(H,39,42)/t22-/m0/s1

Upstream product

• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 71989-26-9 Fmoc-Lys(tert-butoxycarbonyl) 
• 14533-84-7 pentafluorophenyl trifloroacetate 
• 2418-95-3 (S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid 
• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 244633-31-6 pentafluorophenyl 4-nitrobenzenesulfonate 

Downstream Products

• 154130-35-5 N-benzyloxycarbonyl-N'-ε-tert-butoxycarbonyl)-L-lysyl>hydrazine 
• 132776-81-9 5'-O--5-<3-<<2<<6-<<(1,1-dimethylethoxy)carbonyl>amino>-2-<<(9H-fluoren-9-ylmethoxy)carbonyl>amino>-1-oxohexyl>amino>ethyl>-amino>-3-oxopropyl>-2'-deoxyuridine 
• 252570-73-3 C₆₉H₁₀₄N₁₈O₁₅S 
• 252570-79-9 C₈₂H₁₁₅N₂₁O₁₆S 
• 252570-74-4 C₇₁H₁₀₅N₁₉O₁₅S 
• 252570-75-5 C₆₆H₁₀₅N₁₉O₁₆S 
• 252570-77-7 C₇₄H₁₁₀N₂₀O₁₆S 
• 252570-76-6 C₇₄H₁₁₀N₂₀O₁₆S 
• 131152-71-1 Boc-Tyr-D-Met-Phe-Lys(Boc)-Leu-Met-Asp(OBu-t)-NH₂ 
• 131131-18-5 H-Tyr-D-Met-Phe-Lys-Leu-Met-Asp-NH₂ 

Relevant articles and documents

Synthetic approaches to peptides containing the l-Gln-l-Val-D(S)-Dmt motif

The pseudoprolines S-Dmo (5,5-dimethyl-4-oxaproline) and R-Dmt (5,5-dimethyl-4-thiaproline) have been used to study the effects of forcing a fully cis conformation in peptides. Synthesis of peptides containing these (which have the same configuration as l-Pro) is straightforward. However, synthesis of peptides containing S-Dmt is difficult, owing to the rapid cyclisation of l-Aaa-S-Dmt amides and esters to form the corresponding diketopiperazines (DKP); thus the intermediacy of l-Aaa-S-Dmt amides and esters must be avoided in the synthetic sequence. Peptides containing the l-Gln-l-Val-D(S)-Dmt motif are particularly difficult, owing to the insolubility of coupling partners containing Gln. Introduction of Gln as N-Boc-pyroglutamate overcame the latter difficulty and the dipeptide active ester BocPygValOC6F5 coupled in good yield with S-DmtOH. BocPygVal-S- DmtNH(CH2)2C6H4NO2 was converted quantitatively to BocGlnVal-S-DmtNH(CH2)2C6H4NO2 with ammonia, demonstrating the utility of this approach. Two peptide derivatives (CbzSerLysLeuGlnVal-S-DmtNH(CH2)2C6H4NO2 and CbzSerSerLysLeuGlnVal-S- DmtNH(CH2)2C6H4NO2) were assembled, using these new methods of coupling a dipeptide acid active ester with S-DmtOH and introduction of Gln as Pyg, followed by conventional peptide couplings. The presence of the Val caused these peptides to be cleaved very slowly by prostate-specific antigen (PSA) at Leu ↓ Gln, rather than the expected Gln ↓ Val.

PREPARATION OF PENTAFLUOROPHENYL ESTERS OF FMOC PROTECTED AMINO ACIDS WITH PENTAFLUOROPHENYL TRIFLUOROACETATE

A high yield procedure for the preparation of pentafluorophenyl esters of Nα-9-fluorenylmethyloxycarbonyl protected amino acids is described.The procedure utilizes pentafluorophenyl trifluoroacetate.

Preparation and Applications of Pentafluorophenyl Esters of 9-Fluorenylmethyloxycarbonyl Amino Acids for Peptide Synthesis

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