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

Uses

Fmoc-Lys(Boc)-OPfp (CAS# 86060-98-2) is a lysine derivative used in the preparation of motilin-like peptides with gastrointestinal motility-stimulating activity.

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

• 14533-84-7 pentafluorophenyl trifloroacetate 
• 71989-26-9 Fmoc-Lys(tert-butoxycarbonyl) 
• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 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 
• 1028254-31-0 6-[(S)-2-{(S)-6-Amino-2-[(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-hexanoylamino}-3-(4-hydroxy-phenyl)-propionylamino]-hexanoic acid 
• 1027903-88-3 4-[(S)-2-{(S)-6-Amino-2-[(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-hexanoylamino}-3-(4-hydroxy-phenyl)-propionylamino]-butyric acid 
• 1334511-51-1 N⁽²⁾-(9-fluorenylmethoxycarbonyl)-N⁽⁶⁾-tert-butoxycarbonyl-L-lysyl-N-ethyl-S-triphenylmethyl-L-cysteine 
• 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 
• 938076-31-4 N-(N-(N-(N^ε-(1,1-dimethylethoxycarbonyl)-N^α-(O-(1,1-dimethylethyl)-N-(phenylmethoxycarbonyl)-L-seryl)-L-lysyl)-L-leucyl)-L-glutaminyl)-L-valine methyl ester 

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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