- Syntheses of Enantiopure 1,2-Ethylenediamines with Tethered Secondary Amines of the Formula H 2NCH 2CH[(CH 2) nNHMe]NH 2(n = 1-4) from α-Amino Acids: New Agents for Asymmetric Catalysis
-
Tris(hydrochloride) adducts of the title compounds-are prepared from the inexpensive α-amino acids H 2 N(C=O)CH 2 CH(NH 2)CO 2 H, HO(C=O)(CH 2) n ′ CH(NH 2)CO 2 H (n ′ = 1, 2), and H2 N(CH 2) 4 CH(NH 2)CO 2 H, respectively (steps/overall yield = 5/32, 7/30, 7/33, 5/38). The NH 2 group that is remote from the secondary amine is installed via BH 3 reduction of an amide [-(C=O)NR 2[ derived?-from an α-amino carboxylic acid. The MeNHCH 2 units are introduced by BH 3 reductions of alkyl carbamate [RO(C=O)NHCH 2-; R = Et, t-Bu] or amide [MeHN(C=O)-] moieties.
- Kabes, Connor Q.,Gunn, Jack H.,Selbst, Maximilian A.,Lucas, Reagan F.,Gladysz, John A.
-
p. 3277 - 3285
(2020/11/02)
-
- A method of synthesizing L - asparagine (by machine translation)
-
The invention provides a method of synthesizing L - asparagine, the main technical means is to L - aspartic acid as the raw material, first to the reaction in the cauldron the pump enters methanol, then open the reaction kettle, input L - aspartic acid, cooling, subsequently drop adds the chlorination sulfoxide, generating L - aspartic acid methyl ester hydrochloride, then will be of the L - aspartic acid methyl ester hydrochloride into a reaction kettle, then to the reaction in the cauldron the pump enters the ammonia, to obtain the L - asparagine, the method generating L - aspartic acid methyl ester hydrochloride intermediate product, the intermediate product is stable structure, safe and non-toxic, for subsequent operation processing, reaction process only needs to have the participation of ammonia water, reactant complex, the small influence of the product, the method of the invention recovery of the methanol up to 99.5 - 99.9%, not only improving the intermediate the purity of the product, and also avoids the pollution of methanol, L - asparagine is finished effective content of 80 - 85%, moisture content is 15 - 18%, yield and moisture content are higher than the amount of the existing products, the method of the invention is suitable for industrial production. (by machine translation)
- -
-
Paragraph 0018-0020; 0024-0026; 0030-0032; 0036; 0038
(2019/05/08)
-
- COMPLEX
-
PROBLEM TO BE SOLVED: To provide a substance that can be used in a simple quantitative method for desmosines. SOLUTION: In the complex of the present invention, desmosine is bound to a protein directly or via a linking group at the side chain terminal of the 4-position of the pyridine ring of desmosine. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
- -
-
Paragraph 0067-0069
(2019/11/03)
-
- Process for preparing deuterated desmosine and derivatives thereof
-
There is provided a process for preparing a compound represented by the following general formula (1) or a salt thereof, which comprises exchanging one or more of an amino proton in a compound represented by the following general formula (2) or a salt thereof to deuterium, and after the exchanging, converting a deuterium-exchanged compound of the compound represented by the general formula (2) or a salt thereof into the compound represented by the general formula (1) or a salt thereof: wherein, in the general formula (1), one, or two or more of hydrogen atom may be substituted with their isotope; and in the general formula (2), each of R1 is independently hydrogen atom, tert-butyloxycarbonyl group or benzyloxycarbonyl group, and R2 is independently tert-butyl group, benzyl group, methyl group or ethyl group.
- -
-
Page/Page column 6; 9; 10
(2019/05/18)
-
- Synthesis of desmosine-d4: Improvement of isotopic purity by D-H exchange of amino groups
-
Desmosine is a crosslinking pyridinium amino acid of elastin, which is a useful biomarker for the diagnosis of chronic obstructive pulmonary disease (COPD) by LC–MS/MS analysis. We previously reported a synthesis of desmosine-d4, which is useful as an internal standard for quantitative LC–MS/MS analysis of desmosines, by deuterogenation of an alkyne group; however, the isotopic purity of the desmosine-d4was only ca. 50%. The present report describes a new synthesis of desmosine-d4that improves the isotopic purity to ca. 90% by exchanging the protons of the amino groups to deuterium using deuterogenation.
- Watanabe, Daisuke,Suzuki, Rina,Usuki, Toyonobu
-
supporting information
p. 1194 - 1197
(2017/03/02)
-
- Synthesis of desmosine-containing cyclic peptide for the possible elucidation of elastin crosslinking structure
-
Elastin is a vital extracellular matrix protein, which is known for providing elasticity in numerous tissues. It is formed by the self-assembly and subsequent crosslinking of elastin precursor, tropoelastin. Two tetrafunctional, pyridinium-based amino acids desmosine and isodesmosine are exclusively found in elastin and play an important role as crosslinkers. Structural elucidation of elastin has eluded scientists to date, owing to the highly cross-linked structure and insoluble nature. Therefore, in this study, we aimed to synthesize a desmosine-containing cyclic peptide as a partial elastin mimic, in order to eventually facilitate the elucidation of the crosslinking pattern of elastin by mass spectrometric analysis.
- Ogawa, Keita,Hayashi, Takahiro,Lin, Yong Y.,Usuki, Toyonobu
-
p. 3838 - 3847
(2017/06/13)
-
- Facile synthesis of urea-and thiocarbamate-tethered glycosyl beta-amino acids
-
We describe here an efficient way to synthesize series of new urea- and thiocarbamate-tethered glycosyl β-amino acids under mild conditions. These glycosyl β-amino acids are elaborately designed on the basis of natural N-linked glycosides. They have the same side chain length as natural N-glycosyl amino acid while the main chain is replaced with β-amino acid chain. The linkage is an isostere of natural N-linked bond but exhibits competitive stability to chemical and enzymatic hydrolysis. This facile route is benefit from the choice of the commercially available l-aspartic acid as starting material, which not only provides a β-amino acid moiety, but also the α-carboxy group could be transformed to active isocyanate conveniently and economically. The prospective glycosyl β-amino acids are obtained readily by the reaction of isocyanate with appropriately protected glycosylamines and glycosylthiols.
- Teng, Hanbing,Zhang, Zengwei,Zhou, Yifan,Chen, Zhiyong,Chen, Qi,Liu, Yang,Xu, Wenjin
-
p. 71868 - 71872
(2015/09/08)
-
- VERSATILE AND STEREOSPECIFIC SYNTHESIS OF GAMMA,DELTA -UNSATURATED AMINO ACIDS BY WITTIG REACTION
-
The present invention relates to γ,δ-unsaturated a-amino acids of general formula (I). The present invention also provides a versatile process for the stereospecific synthesis of said compounds of formula (I), involving a Wittig reaction. The present invention also relates to intermediate products of general formulae (II) and (III), as shown below, which are involved in the synthesis of compounds (I).
- -
-
Paragraph 30
(2013/03/28)
-
- PROCESSES FOR PREPARING AMINO-SUBSTITUTED GAMMA-LACTAMS
-
The present application describes general process for the preparation of amino-substitued gamma-lactams involving the reaction of synthons of the general Formulae (I) and (VI): with amines. The processes are amenable to solid phase synthetic techniques and therefore allow the efficient incorporation of amino-substitued gamma-lactams into a wide variety of structural scaffolds, including, in particular peptides.
- -
-
Page/Page column 35; 36; 37
(2010/10/03)
-
- Method of inhibiting protein tyrosine phosphatase 1B and/or T-cell protein tyrosine phosphatase 4 and/or other PTPases with an Asp residue at position 48
-
The present invention provides a method of inhibiting a member of a family of Protein Tyrosine Phosphatases (PTPases, PTPs) such as PTP1B, TC-PTP, CD45, SHP-1, SHP-2, PTPα, PTPε, PTPμ, PTPδ, PTPσ, PTPζ, PTPβ, PTPD1, PTPD2, PTPH1, PTP-MEG1, PTP-LAR, and HePTP by exposing said Ptpase member by administration to a host or otherwise to at least one compound with certain structural, physical and spatial characteristics that allow for the interaction of said compound with specific residues of the active site of PTP1B and/or TC-PTP. These compounds are indicated in the management or treatment of a broad range of diseases such as autoimmune diseases, acute and chronic inflammation, osteoporosis, various forms of cancer and malignant diseases, and type I diabetes and type II diabetes, as well as in the isolation of PTPases and in elucidation or further elucidation of their biological function.
- -
-
Page/Page column 108-110
(2010/11/23)
-
- Difluoromethylene analogues of aspartyl phosphate: The first synthetic inhibitors of aspartate semi-aldehyde dehydrogenase
-
The difluoromethylene analogue of aspartyl phosphate 6 has been prepared by the fluoride catalysed coupling of diethyl trimethyisilyldifluoromethyl phosphonate with an appropriate aldehyde followed by Dess-Martin oxidation and deprotection; the deprotected compound inhibited (K1 95 μM) aspartate semi-aldehyde dehydrogenase, a key enzyme involved in bacterial amino acid and peptidoglycan biosynthesis.
- Cox,Hadfield,Belen Mayo-Martin
-
p. 1710 - 1711
(2007/10/03)
-
- Synthesis and in vitro enzyme activity of aza, oxa and thia derivatives of bacterial cell wall biosynthesis intermediates
-
Mechanism based inhibitors of diaminopimelate aminotransferase (DAP-AT) were designed using knowledge of its substrate specificity and mechanism. Synthesis of thiolester and amide substrate analogues was achieved prior to in vitro inhibition studies, but ester analogues proved too unstable to isolate. Thia substrate analogues showed no inhibitory properties, but the aza substrate analogue 12a showed reversible inhibition vs. DAP-AT and time dependent inhibition in the absence of the natural substrate 4. Substrate analogue 12a is thefirst example of an amide inhibitor of PLP dependent enzymes. Antibiotic properties of 12a were also briefly assessed.
- Cox,Wang
-
p. 2022 - 2034
(2007/10/03)
-
- Asymmetric Amino Acid Synthesis: Preparation of the β Anion derived from Aspartic Acid
-
(S)-1-t-Butyl 4-methyl N-benzyloxycarbonylaspartate (5a), and (S)-1-t-butyl 4-allyl N-benzyloxycarbonylaspartate (5b) have been synthesized from (S)-aspartic acid (2), and can be readily alkylated and hydroxyalkylated at the β-carbon for asymmetric amino acid synthesis.
- Baldwin, Jack E.,Moloney, Mark G.,North, Michael
-
p. 833 - 834
(2007/10/02)
-
- Synthesis of Stereospecific Deuterium-Labeled Homoserines and Homoserine Lactones
-
The syntheses of the stereospecific deuteriated derivatives (2S,4R)- and (2S,4S)-2H>homoserine lactone hydrochlorides, (2S,3R)-2H>- and (2S,3S)-2H2>homoserine lactone hydrochlorides, and (2S,3R,4R)-2H2>- and (2S,3S,4S)-2H3>homoserine lactone hydrochlorides as well as the homoserine derivatives themselves have been synthesized in eight simple steps from the appropriate aspartic acids via a route designed for maximal synthetic versatility.The enantiomeric excesses at carbon 4 of the deuteriated homoserines are R = 78percent (98percent 2H) and S = 82percent (98percent 2H) and at carbon 3 R = 100percent (98percent 2H2) and S = 100percent (95percent2H).
- Ramalingam, Kondareddiar,Woodard, Ronald W.
-
p. 1900 - 1903
(2007/10/02)
-
- Synthesis of a Monocyclic β-Lactam Stereospecifically Labelled at C-4
-
In connection with biosynthetic studies, the β-lactams (5; 4-HR = 2H) and (5; 3-H = 4-HS = 2H) have been synthesized.The 1H and 2H n.m.r. spectra of these compounds confirm the assignment of the stereochemistry to the two hydrogens at C-4 of monocyclic β-lactams such as nocardicin A.Samples of the amino-acid L-asparagine stereospecifically labelled at C-3 have been made in the course of this work.
- Gani, David,Young, Douglas W.,Carr, David M.,Poyser, J. Philip,Sadler, Ian H.
-
p. 2811 - 2814
(2007/10/02)
-
