Fmoc-2,3-dehydro-Valine
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Fmoc-2,3-dehydro-Valine

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Category
Fmoc-Amino Acids
Catalog number
BAT-008945
CAS number
198546-38-2
Molecular Formula
C20H19NO4
Molecular Weight
337.4
Fmoc-2,3-dehydro-Valine
IUPAC Name
2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbut-2-enoic acid
Synonyms
Fmoc-Val(2,3-dehydro)-OH; Fmoc-2,3-dehydroval-OH; Fmoc-2,3-dehydro-Val-OH; Fmoc-α,β-dehydro-Val-OH
Appearance
White solid
Purity
≥ 99% (HPLC)
Density
1.3±0.1 g/cm3
Boiling Point
553.2±42.0 °C at 760 mmHg
InChI
InChI=1S/C20H19NO4/c1-12(2)18(19(22)23)21-20(24)25-11-17-15-9-5-3-7-13(15)14-8-4-6-10-16(14)17/h3-10,17H,11H2,1-2H3,(H,21,24)(H,22,23)
InChI Key
IYVIIHAWJFLOAR-UHFFFAOYSA-N
Canonical SMILES
CC(=C(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C
1. New concept for long-acting insulin: spontaneous conversion of an inactive modified insulin to the active hormone in circulation: 9-fluorenylmethoxycarbonyl derivative of insulin
E Gershonov, Y Shechter, M Fridkin Diabetes. 1999 Jul;48(7):1437-42. doi: 10.2337/diabetes.48.7.1437.
Insulin is a short-lived species in the circulatory system. After binding to its receptor sites and transmission of its biological signals, bound insulin undergoes receptor-mediated endocytosis and consequent degradation. An inactive insulin derivative that is not recognized by the receptor has a longer circulation life, but obviously is biologically impotent. (Fmoc)2 insulin is an insulin derivative purified through high-performance liquid chromatography in which two 9-fluorenylmethoxycarbonyl (Fmoc) moieties are covalently linked to the (alpha-amino group of phenylalanine B1 and the epsilon-amino group of lysine B29. It has 1-2% of the biological potency and receptor binding capacity of the native hormone. After incubation, (Fmoc)2 insulin undergoes a time-dependent spontaneous conversion to fully active insulin in aqueous solution at 37 degrees C and a pH range of 7-8.5. At pH 7.4, the conversion proceeds slowly (t1/2 = 12 +/- 1 days) and biological activity is generated gradually. A single subcutaneous administration of (Fmoc)2 insulin to streptozocin-treated diabetic rats normalized their blood glucose levels and maintained the animals in an anabolic state over 2-3 days. A broad shallow peak of immunoreactive insulin was found to persist in circulation over this period. To confirm further that the long-acting effect of (Fmoc)2 insulin proceeds via slow release in the blood circulation itself, we administered native insulin, NPH insulin, or the (Fmoc)2 derivative intraperitoneally. The rats recovered from hypoglycemia at t1/2 = 8.0 +/- 0.3 and 10 +/- 0.4 h after administration of native and NPH insulin, respectively. In contrast, (Fmoc)2 insulin was active for a significantly longer time, with an extended onset of t1/2 = 26 +/- 1h, and a glucose-lowering effect even 40 h after administration. (Fmoc)2 insulin was also found to be more resistant to proteolysis. Finally, we found that (Fmoc)2 insulin does not induce antigenic effects. In summary, we present here a new concept for prolonging the half-life of insulin in the circulatory system, in which receptor-mediated endocytosis and degradation is delayed and accompanied by a time-dependent generation of basal insulin.
2. Fmoc-2-mercaptobenzothiazole, for the introduction of the Fmoc moiety free of side-reactions
Albert Isidro-Llobet, Xavier Just-Baringo, Ariel Ewenson, Mercedes Alvarez, Fernando Albericio Biopolymers. 2007;88(5):733-7. doi: 10.1002/bip.20732.
A double side-reaction, consisting in the formation of Fmoc-beta-Ala-OH and Fmoc-beta-Ala-AA-OH, during the preparation of Fmoc protected amino acids (Fmoc-AA-OH) with Fmoc-OSu is discussed. Furthermore, the new Fmoc-2-MBT reagent is proposed for avoiding these side-reactions as well as the formation of the Fmoc-dipeptides (Fmoc-AA-AA-OH) and even tripeptides, which is another important side-reaction when chloroformates such as Fmoc-Cl is used for the protection of the alpha-amino function of the amino acids.
3. Preparative Method for Asymmetric Synthesis of ( S)-2-Amino-4,4,4-trifluorobutanoic Acid
Jianlin Han, Ryosuke Takeda, Xinyi Liu, Hiroyuki Konno, Hidenori Abe, Takahiro Hiramatsu, Hiroki Moriwaki, Vadim A Soloshonok Molecules. 2019 Dec 10;24(24):4521. doi: 10.3390/molecules24244521.
Enantiomerically pure derivatives of 2-amino-4,4,4-trifluorobutanoic acid are in great demand as bioisostere of leucine moiety in the drug design. Here, we disclose a method specifically developed for large-scale (>150 g) preparation of the target (S)-N-Fmoc-2-amino-4,4,4-trifluorobutanoic acid. The method employs a recyclable chiral auxiliary to form the corresponding Ni(II) complex with glycine Schiff base, which is alkylated with CF3-CH2-I under basic conditions. The resultant alkylated Ni(II) complex is disassembled to reclaim the chiral auxiliary and 2-amino-4,4,4-trifluorobutanoic acid, which is in situ converted to the N-Fmoc derivative. The whole procedure was reproduced several times for consecutive preparation of over 300 g of the target (S)-N-Fmoc-2-amino-4,4,4-trifluorobutanoic acid.
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