Fmoc-Nω-(2,2,5,7,8-pentamethyl-chromane-6-sulfonyl)-L-β-homoarginine
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Fmoc-Nω-(2,2,5,7,8-pentamethyl-chromane-6-sulfonyl)-L-β-homoarginine

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Category
β−Amino acids
Catalog number
BAT-002077
CAS number
700377-76-0
Molecular Formula
C36H44N4O7S
Molecular Weight
676.84
IUPAC Name
(3S)-6-[[amino-[(2,2,5,7,8-pentamethyl-3,4-dihydrochromen-6-yl)sulfonylamino]methylidene]amino]-3-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid
Synonyms
Fmoc-L-β-HomoArg(Pmc)-OH; (3S)-6-[[Amino-[(2,2,5,7,8-pentamethyl-3,4-dihydrochromen-6-yl)sulfonylamino]methylidene]amino]-3-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid
Appearance
White solid
Purity
≥ 98% (HPLC)
Storage
Store at 2-8 °C
InChI
InChI=1S/C36H44N4O7S/c1-21-22(2)33(23(3)25-16-17-36(4,5)47-32(21)25)48(44,45)40-34(37)38-18-10-11-24(19-31(41)42)39-35(43)46-20-30-28-14-8-6-12-26(28)27-13-7-9-15-29(27)30/h6-9,12-15,24,30H,10-11,16-20H2,1-5H3,(H,39,43)(H,41,42)(H3,37,38,40)/t24-/m0/s1
InChI Key
MGKMEQWQKICWRD-DEOSSOPVSA-N
Canonical SMILES
CC1=C(C(=C(C2=C1OC(CC2)(C)C)C)S(=O)(=O)NC(=NCCCC(CC(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)N)C
1. Longitudinal Outcomes for Multisystem Inflammatory Syndrome in Children
Kanwal M Farooqi, et al. Pediatrics. 2021 Aug;148(2):e2021051155. doi: 10.1542/peds.2021-051155. Epub 2021 Jul 15.
Background: In spring 2020, a novel hyperinflammatory process associated with severe acute respiratory syndrome coronavirus 2 multisystem inflammatory syndrome in children (MIS-C) was described. The long-term impact remains unknown. We report longitudinal outcomes from a New York interdisciplinary follow-up program. Methods: All children 2.5). Whereas most inflammatory markers normalized by 1 to 4 weeks, 32% (n = 11 of 34) exhibited persistent lymphocytosis, with increased double-negative T cells in 96% of assessed patients (n = 23 of 24). By 1 to 4 weeks, only 18% (n = 7 of 39) had mild echocardiographic findings; all had normal coronaries. At 1 to 4 months, the proportion of double-negative T cells remained elevated in 92% (median 9%). At 4 to 9 months, only 1 child had persistent mild dysfunction. One had mild mitral and/or tricuspid regurgitation. Conclusions: Although the majority of children with MIS-C present critically ill, most inflammatory and cardiac manifestations in our cohort resolved rapidly.
2. Reduction of 8a-hydroxy-2,2,5,7,8-pentamethyl-6-chromanone
Indrajati Kohar, Peter T Southwell-Keely Redox Rep. 2002;7(5):251-5. doi: 10.1179/135100002125000730.
Two-electron oxidation of 2,2,5,7,8-pentamethyl-6-chromanol (PH), a model compound of alpha-tocopherol, gives the unstable 8a-hydroxy-2,2,5,7,8-pentamethyl-6-chromanone (POH) which rearranges to form stable 2-(3-hydroxy-3-methylbutyl)-3,5,6-trimethyl-1,4-benzoquinone (PQ). POH and PQ are isomers which have the same oxidation state. The aim of this work was to compare the ease of reduction of POH and PQ at room temperature using a variety of biological and chemical reductants in a reductant:POH (PQ) ratio of 20:1 (or 16:1). Ascorbic acid completely reduced POH to PH in 20 min, but had no effect on PQ after 40 min. Sodium ascorbate did not reduce POH or PQ at all after 40 min. Sodium dithionite reduced POH to PH (85%) in 20 min, but reduced PQ to its hydroquinone, PQH2 (67%) in 40 min. Dithiothreitol produced a slight reduction of POH to PH (21%) but reduced PQ to PQH2 (69%). NADH/FAD reduced POH and PQ to PQH2 (73% and 42%, respectively) in 10 min. It was concluded that POH is easier to reduce than PQ and more likely to form PH as a product, particularly under conditions of mild acidity.
3. Oxidation of the α-tocopherol model compound 2,2,5,7,8-pentamethyl-6-chromanol in the presence of alcohols
C Suarna, M Baca, P T Southwell-Keely Lipids. 1992 Jun;27(6):447-53. doi: 10.1007/BF02536387.
Oxidation of the vitamin E model compound, 2,2,5,7,8-pentamethyl-6-chromanol (1b) byt-butyl hydroperoxide in chloroform has been studied in the presence of ethanol, heptanol and cholesterol. In the absence of an alcohol, the major products were the spirodimer (13b) and spirotrimer (14b) of 1b, together with 1H,2,3-dihydro-3,3,5,6,9,10,11a(R)-heptamethyl-7a(S)-(3-hydroxy-3-methylbutyl)-pyrano[2,3-a] xanthene 8(7aH), 11(11aH) dione (6b). In the presence of ethanol, heptanol and cholesterol, the major products were 5-ethoxymethyl-2,2,7,8-tetramethyl-6-chromanol (16b), 5-heptoxymethyl-2,2,7,8-tetramethyl-6-chromanol (17) and 5-cholesteroxymethyl-2,2,7,8-tetramethyl-6-chromanol (18). However, when water was present in a homogeneous reaction, the most rapidly formed product was 2-(3-hydroxy-3-methylbutyl)-3,5,6-trimethyl-1,4-benzoquinone (5b). Compounds 13b, 14b, 16b, 17 and 18 are formedvia a quinone methide intermediate, and compound 5b is formedvia a phenoxylium ion. The phenoxylium species appears to be the preferred intermediate when water is present, whereas the quinone methide species is prefered in the absence of water.
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