111662-65-8 Usage
Description
FMOC-D-GLA(OTBU)2-OH is a protected form of carboxyglutamic acid, which is an essential component in the synthesis of peptides and peptide fragments. It is characterized by its unique chemical structure, featuring a carboxylic acid group and a D-glutamic acid residue. The presence of the Fmoc (9-fluorenylmethoxycarbonyl) group and two tert-butyl (tBu) protecting groups ensures the stability and reactivity of the molecule during the synthetic process.
Uses
Used in Pharmaceutical Industry:
FMOC-D-GLA(OTBU)2-OH is used as a key intermediate in the synthesis of cyclic RGD pentapeptides, which are known for their potential applications in various therapeutic areas, such as cancer treatment, cardiovascular diseases, and tissue engineering. The cyclic RGD pentapeptides are designed to target specific cell surface receptors, such as integrins, to modulate cell adhesion, migration, and proliferation.
Used in Peptide Synthesis:
FMOC-D-GLA(OTBU)2-OH is used as a building block in the solid-phase peptide synthesis (SPPS) process. The Fmoc group serves as a protecting group for the carboxylic acid, allowing for selective deprotection and coupling reactions during the synthesis of longer peptide chains. The tBu groups protect the side chain of the D-glutamic acid residue, preventing unwanted side reactions and ensuring the correct formation of the desired peptide sequence.
Used in Research and Development:
FMOC-D-GLA(OTBU)2-OH is utilized in the development of novel peptide-based drugs and therapeutic agents. Researchers use this protected carboxyglutamic acid derivative to explore new peptide sequences and structures with potential biological activities, such as antimicrobial, antiviral, or immunomodulatory properties. The versatility of FMOC-D-GLA(OTBU)2-OH enables the design and synthesis of a wide range of peptide-based molecules for various applications in the pharmaceutical and biotechnology industries.
Check Digit Verification of cas no
The CAS Registry Mumber 111662-65-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,1,6,6 and 2 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 111662-65:
(8*1)+(7*1)+(6*1)+(5*6)+(4*6)+(3*2)+(2*6)+(1*5)=98
98 % 10 = 8
So 111662-65-8 is a valid CAS Registry Number.
InChI:InChI=1/C29H35NO8/c1-28(2,3)37-25(33)21(26(34)38-29(4,5)6)15-23(24(31)32)30-27(35)36-16-22-19-13-9-7-11-17(19)18-12-8-10-14-20(18)22/h7-14,21-23H,15-16H2,1-6H3,(H,30,35)(H,31,32)/t23-/m1/s1
111662-65-8Relevant articles and documents
Improved chemical synthesis of optically pure N-(9-fluorenylmethoxycarbonyl)-γ,γ′-di-tert-butyl-γ- carboxyglutamic acid
Somlai, Csaba,Penke, Botond,Peter, Antal
, p. 464 - 466 (1997)
-
A practical synthesis of fully protected L-γ-carboxyglutamic acid
Jiang, Sheng,Lai, Christopher C.,Kelley, James A.,Roller, Peter P.
, p. 23 - 25 (2007/10/03)
We have developed a new synthetic route for the preparation of Fmoc protected L-γ-carboxyglutamic acid in 60% overall yield (>99% ee) via a six-step synthesis from D-Garner's aldehyde. An aldol condensation and the selective cleavage of the acetonide prot
The synthesis and properties of Gla- and Phe-containing analogues of cyclic RGD pentapeptides
Davies, John S.,Enjalbal, Christine,Nguyen, Corrine,Al-Jamri, Loai,Naumer, Christian
, p. 2907 - 2915 (2007/10/03)
Cyclopentapeptides containing the Arg-Gly-Asp motif have been synthesised using solid-phase assembly of side-chain-protected linear precursors, followed by solution-phase cyclisation. The replacement of the Asp residue by γ-carboxyglutamic acid (Gla) is a novel feature which gives rise to an analogue which inhibits cell adhesion, yet its congeners do not show activity in binding assays with recombinant integrin receptors. NMR techniques support a β/γ-turn conformation in most of the analogues. The Royal Society of Chemistry 2000.
