- Phenyl Glycolipids with Different Glycosyl Groups Exhibit Marked Differences in Murine and Human iNKT Cell Activation
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Glycosphingolipids (GSLs) bearing the α-galactosyl headgroup and the acyl chain terminated with a phenyl derivative were found to be more potent than α-galactosyl ceramide (αGalCer) to stimulate both murine and human invariant natural killer T (iNKT) cells and to induce an antibody isotope switch to IgG. In this study, we replaced the galactosyl group with glucose (αGlc) and its fluoro-analogs and found that phenyl GSLs with αGlc (C34-Glc) and its fluoro-analog 6F-C34-Glc were stronger than those with αGal in stimulating human iNKT cells but weaker in mice. Their activities have a strong correlation with the binding avidities of the ternary interaction between the iNKT-cell receptor (iNKTCR) and CD1d-GSL complex. It was the iNKTCR rather than CD1d that dictated the species-specific responses. C34-Glc was further used as an adjuvant for a SSEA4-crm-197 vaccine, and after immunization in mice, the vaccine was highly effective against Lewis lung carcinoma.
- Wu, Tai-Na,Lin, Kun-Hsien,Wu, Ying-Ta,Huang, Jing-Rong,Hung, Jung-Tung,Wu, Jen-Chine,Chen, Chien-Yu,Chu, Kuo-Ching,Lin, Nan-Horng,Yu, Alice L.,Wong, Chi-Huey
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Read Online
- Practical synthesis of KRN7000 from phytosphingosine
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The efficient and practical synthesis of die biologically important a-galactosylceramides, KRN7000, from phytosphingosine has been achieved in six steps in high overall yield.
- Kim, Sanghee,Song, Soyoung,Lee, Taeho,Jung, Sungkyu,Kim, Deukjoon
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- Synthesis of tritium labeled KRN7000
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The synthesis of a multiple tritiated analog of KRN7000 (α-galactosyl ceramide) is described, enabling further studies to quantitate the affinity of KRN7000 for its receptor and to study its pharmacokinetic properties.
- Risseeuw, Martijn D.P.,Berkers, Celia R.,Ploegh, Hidde L.,Ovaa, Huib
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Read Online
- An Efficient and Concise Synthesis of α-Galactosylceramide
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A concise and stereoselective synthesis of α-galactosylceramide (α-GalCer) is described. The key features of the synthetic strategy are the use of a phytosphingosine in which the amine is masked as a tetrachlorophthalimide and the diol as an isopropylidene acetal, and the galactosyl donor is protected as a 4,6-benzylidene to improve the α selectivity of the glycosylation reaction. The pattern of protecting groups on the donor and the acceptor have proven to give an excellent match of reactivity, allowing the glycosylation reaction to take place stereoselectively. The overall synthesis gave α-GalCer in good yields and in few steps.
- Imperio, Daniela,Morelli, Laura,Compostella, Federica,Panza, Luigi
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- Synthetic preparation and immunological evaluation of β-mannosylceramide and related: N -acyl analogues
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The synthesis of the invariant natural killer (iNK) T cell agonist β-mannosylceramide along with a series of fatty amide analogues is reported. Of the six β-glycosylation protocols investigated, the sulfoxide methodology developed by Crich and co-workers proved to be the most effective where the reaction of a mannosyl sulfoxide and phytosphingosine derivative gave a key glycolipid intermediate as a 95:5 mixture of β- to α-anomers in high yield. A series of mannosyl ceramides were evaluated for their ability to activate D32.D3 NKT cells and induce antitumour activity.
- Berzofsky, Jay A.,Compton, Benjamin J.,Larsen, David S.,Painter, Gavin F.,Robinson, Sage A.,Terabe, Masaki,Yau, Jessica
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- Direct and efficient glycosylation protocol for synthesizing α-glycolipids: Application to the synthesis of KRN7000
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Herein we describe a simple and practical protocol for accessing the biologically active galactosyl ceramide KRN7000 and other α-glycolipids with excellent yield and stereoselectivity by using per-O-silylated galactosyl iodide and stannyl ethers as glycosylation partners. This direct glycosylation reaction reduces the overall number of steps and provides rapid access to biologically important α-galactosyl ceramide derivatives. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Boutureira, Omar,Morales-Serna, Jose Antonio,Diaz, Yolanda,Matheu, M. Isabel,Castillon, Sergio
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Read Online
- A comparison of benzyl and 2-naphthylmethyl ethers as permanent hydroxyl protecting groups in the synthesis of α-galactoglycosphingolipids KRN7000 and PBS-57
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Due to the interest in the biological properties of marine derived α-galactoglycosphingolipids (α-GalGSLs), a lot of work has focused on the development of their synthesis. Here we conducted the direct comparison of benzyl and 2-naphthylmethyl (Nap) ether
- Yao, Dongming,Liu, Yichu,Gao, Qi,Sui, Qiang,Liu, Xiaoping,Ding, Ning
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Read Online
- A practical and scalable synthesis of KRN7000 using glycosyl iodide as the glycosyl donor
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KRN7000 is particularly useful because it is a powerful and specific CD1d agonist and has prompted intense interest in the context of immunology in the past 25 years. Its limited commercial availability and high price has led to the publication of many different syntheses. However, almost all of them focused on the methodology development rather than a scalable synthesis. Herein, we have described a practical and scalable procedure for the synthesis of KRN7000 basing on the glycosyl iodide method. This procedure involves total of eight steps to obtain the highly pure product KNR7000 on gram scale from the commercially available starting materials (d-galactose and the phytosphingosine) with only three column chromatographic purifications.
- Zhang, Yang,Guo, Jia,Xu, Xiaoyan,Gao, Qi,Liu, Xianglai,Ding, Ning
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p. 248 - 252
(2020/11/30)
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- Potent Neutralizing Antibodies Elicited by RBD-Fc-Based COVID-19 Vaccine Candidate Adjuvanted by the Th2-Skewing iNKT Cell Agonist
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The development of a safe and effective COVID-19 vaccine is of paramount importance to terminate the current pandemic. An adjuvant is crucial for improving the efficacy of the subunit COVID19 vaccine. α-Galactosylceramide (αGC) is a classical iNKT cell agonist which causes the rapid production of Th1- and Th2-associated cytokines; we, therefore, expect that the Th1- or Th2-skewing analogues of αGC can better enhance the immunogenicity of the receptor-binding domain in the spike protein of SARS-CoV-2 fused with the Fc region of human IgG (RBD-Fc). Herein, we developed a universal synthetic route to the Th1-biasing (α-C-GC) and Th2-biasing (OCH and C20:2) analogues. Immunization of mice demonstrated that αGC-adjuvanted RBD-Fc elicited a more potent humoral response than that observed with Alum and enabled the sparing of antigens. Remarkably, at a low dose of the RBD-Fc protein (2 μg), the Th2-biasing agonist C20:2 induced a significantly higher titer of the neutralizing antibody than that of Alum.
- Chen, Xiang-Zhao,Gao, Xiao-Fei,Guo, Jun,He, Na,Liu, Zheng,Luo, Rui,Wang, Xi-Feng,Wang, Ya-Cong,Yan, Cheng,Zhang, Meng-Jia
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p. 11554 - 11569
(2021/07/31)
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- GLYCOPEPTIDE VACCINE
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The present invention generally relates to a glycopeptide conjugate compound of Formula (I):, as described herein, compositions comprising the conjugate compound and to the use of such a compound to as a vaccine.
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- A versatile synthesis of αGalCer and its analogues exploiting a cyclic carbonate as phytosphingosine 3,4-diol protecting group
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A convenient synthetic strategy to αGalCer and some relevant analogues by using a handily protected phytosphingosine is reported here. The conversion of the phytosphingosine amino group to azide and the protection of 3,4-diol as cyclic carbonate group, cl
- Panza, Luigi,Compostella, Federica,Imperio, Daniela
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- HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS
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Glycosphingolipids (GSLs) compositions and methods for iNKT-independent induction of chemokines are disclosed.
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- HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS WITH ALTERED GLYCOSYL GROUPS
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Glycosphingolipids (GSLs) bearing α-glucose (α-Glc) that preferentially stimulate human invariant NKT (iNKT) cells are provided. GSLs with α-glucose (α-Glc) that exhibit stronger induction in humans (but weaker in mice) of cytokines and chemokines and exp
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- NKT cell-dependent glycolipid-peptide vaccines with potent anti-tumour activity
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It is known that T cells can eliminate tumour cells through recognition of unique or aberrantly expressed antigens presented as peptide epitopes by major histocompatibility complex (MHC) molecules on the tumour cell surface. With recent advances in defini
- Anderson, Regan J.,Compton, Benjamin J.,Tang, Ching-Wen,Authier-Hall, Astrid,Hayman, Colin M.,Swinerd, Gene W.,Kowalczyk, Renata,Harris, Paul,Brimble, Margaret A.,Larsen, David S.,Gasser, Olivier,Weinkove, Robert,Hermans, Ian F.,Painter, Gavin F.
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p. 5120 - 5127
(2015/08/24)
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- Concise synthesis of α-galactosyl ceramide from d-galactosyl iodide and d-lyxose
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α-Galactosyl ceramide is synthesized from d-lyxose in 32% overall yield in five steps. The short and efficient protocol involves a one-pot protection and glycosidation of d-lyxose with d-galactosyl iodide as a key step. The α-linked disaccharide obtained was subsequently transformed into α-galactosyl ceramide in four steps involving Z-selective Wittig olefination at C-1, stereo-inversion at C-4 using azide, one-pot reduction of azide and amidation, and global deprotection.
- Yen, Yu-Fen,Kulkarni, Suvarn S.,Chang, Chun-Wei,Luo, Shun-Yuan
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- Synthesis and biological evaluation of antifungal activities of novel 1,2-trans glycosphingolipids
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The synthesis and in-vitro biological evaluation of antifungal activities of a series of 1,2-trans glycosphingolipids (GSL) against Candida albicans, Candida parapsilosis, and Candida tropicalis were described. The preliminary study indicated that the sor
- Ding, Ning,Zhang, Wei,Lv, Guokai,Li, Yingxia
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experimental part
p. 786 - 793
(2012/03/08)
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- Asymmetric synthesis of the α-D-galactosyl ceramide KRN7000 via an organocatalytic aldol reaction as key step
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The asymmetric synthesis of the antitumor and immunostimulatory α-D-galactosyl ceramide KRN7000 using a (R)-proline-catalyzed enantioselective aldol reaction as key step is described. The title compound is synthesized in thirteen linear steps with excelle
- Enders, Dieter,Terteryan, Violeta,Paleek, Jii
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experimental part
p. 2979 - 2984
(2010/10/05)
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- Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→2) galactosyl ceramide
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We herein report a faster and less cumbersome synthesis of the biologically attractive, α-galactosyl ceramide (α-GalCer), known as KRN7000, and its analogues. More importantly, the use of a silicon tethered intramolecular glycosylation reaction gave easy
- Veerapen, Natacha,Brigl, Manfred,Garg, Salil,Cerundolo, Vincenzo,Cox, Liam R.,Brenner, Michael B.,Besra, Gurdyal S.
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scheme or table
p. 4288 - 4291
(2010/04/26)
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- Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand
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KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release Th1 and Th2 cytokines. In an effort to understand the structure-activity relationships, we have carried out the synthesis of a c
- Park, Jeong-Ju,Lee, Ji Hyung,Ghosh, Subhash C.,Bricard, Gabriel,Venkataswamy, Manjunatha M.,Porcelli, Steven A.,Chung, Sung-Kee
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scheme or table
p. 3906 - 3909
(2009/04/06)
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- Synthesis of α-galactosyl ceramide (KRN7000) and analogues thereof via a common precursor and their preliminary biological assessment
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(Chemical Equation Presented) A new practical synthesis of α-GalCer and of its analogues is presented, opening the chance to easily modify the sphingosine chain. The common precursor is a disaccharide, obtained by coupling tetra-O-benzyl-D-galactose with allyl 2,3-O-isopropylidene-D-lyxofuranoside. Introduction of alkyl chains via Wittig reaction (for α-GalCer and OCH) or via Williamson reaction (for oxa analogues) followed by standard synthetic steps allows one to efficiently obtain such compounds. The analogues are able to activate iNKT cells when presented by CD1d expressing cells.
- Michieletti, Mario,Bracci, Antonio,Compostella, Federica,De Libero, Gennaro,Mori, Lucia,Fallarini, Silvia,Lombardi, Grazia,Panza, Luigi
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supporting information; body text
p. 9192 - 9195
(2009/04/11)
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- Concise syntheses of immunostimulating glycolipids, α-galactosyl ceramides
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α-Galactosylceramides (α-GalCers) are well known as immunostimulating agents having therapeutic potential. To facilitate the synthesis of α-GalCers and their derivatives, a novel and convergent strategy was designed, which is expected to be versatile for the preparation of a variety of analogues in a diversity-oriented fashion. As an initial demonstration of our strategy, KRN7000 and OCH were synthesized in eight steps from a common intermediate, which is easily obtainable in a multi-gram scale.
- Tsujimoto, Takashi,Ito, Yukishige
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p. 5513 - 5516
(2008/02/10)
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- Concise synthesis of clarhamnoside, a novel glycosphingolipid isolated from the marine sponge Agela clathrodes
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The first total synthesis of a novel α-galactoglycosphingolipid clarhamnoside has been achieved through a straightforward strategy. A thiogalactosyl donor with a benzylidene group at C-4 and C-6 and nonparticipating p-methoxybenzyl group at C-2 was succes
- Ding, Ning,Li, Chunxia,Liu, Yunpeng,Zhang, Zaihong,Li, Yingxia
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p. 2003 - 2013
(2008/02/10)
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- A concise synthesis of tetrahydroxy-LCB, α-galactosyl ceramide, and 1,4-dideoxy-1,4-imino-L-ribitol via D-allosamines as key building blocks
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The total syntheses of tetrahydroxy-LCB 1, α-galactosyl ceramide 2, and 1,4-dideoxy-1,4-imino-L-ribitol 3 via D-allosamine derivatives as common synthons are described here.
- Luo, Shun-Yuan,Kulkarni, Suvarn S.,Chou, Chien-Hung,Liao, Wei-Meen,Hung, Shang-Cheng
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p. 1226 - 1229
(2007/10/03)
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- GLYCOLIPIDS AND ANALOGUES THEREOF AS ANTIGENS FOR NK T CELLS
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This invention relates to immunogenic compounds which may serve as ligands for NKT (natural killer T) cells and to methods of use thereof in modulating immune responses.
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Page/Page column 75-76; 4/23
(2008/06/13)
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- Synthesis and biological evaluation of α-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3)
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Glycoceramides can activate NKT cells by binding with CD1d to produce IFN-γ, IL-4, and other cytokines. An efficient synthetic pathway for α-galactosylceramide (KRN7000) was established by coupling a protected galactose donor to a properly protected ceramide. During the investigation, it was discovered that when the ceramide was protected with benzyl groups, only β-galactosylceramide was produced from the glycosylation reaction. In contrast, the ceramide with benzoyl protecting groups produced α-galactosylceramide. Isoglobotrihexosylceramide (iGb3) was prepared by glycosylation of Galα1-3Galβ1-4Glc donor with 2-azido-sphingosine in high yield. Biological assays on the synthetic KRN7000 and iGb3 were performed using human and murine iNKT cell clones or hybridomas.
- Xia, Chengfeng,Yao, Qingjia,Schuemann, Jens,Rossy, Emmanuel,Chen, Wenlan,Zhu, Lizhi,Zhang, Wenpeng,De Libero, Gennaro,Wang, Peng George
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p. 2195 - 2199
(2007/10/03)
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- Novel synthesis of α-galactosyl-ceramides and confirmation of their powerful NKT cell agonist activity
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α-Galactosyl-ceramide (1) has been identified as a powerful modulator of immunological processes through its capacity to bind CD1d molecules and specifically activate invariant natural killer (NK)-like T cells (iNKT cells). This paper describes the synthe
- Lee, Adrianne,Farrand, Kathryn J.,Dickgreber, Nina,Hayman, Colin M.,Juers, Stefan,Hermans, Ian F.,Painter, Gavin F.
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p. 2785 - 2798
(2007/10/03)
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- HEPATITIS C VIRUS INHIBITOR COMPRISING ALPHA-GLYCOSYLCERAMIDE AS THE ACTIVE INGREDIENT
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This invention provides a growth inhibitor of human hepatitis C virus comprising, as an active ingredient, α-glycosylceramide used for patients infected with the aforementioned viruses. This inhibitor of hepatitis C virus comprises, as an active ingredien
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Page/Page column 16
(2010/02/11)
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- Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes
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Phytosphingosine and its short-chain analog were efficiently synthesized with 19% overall yield in 10 steps, respectively, starting from an inexpensive d-lyxose. Galactosyl donors of sulfide and phosphite types bearing benzoyl protecting groups of 4- and
- Fan, Gang-Ting,Pan, Yi-Shin,Lu, Kuo-Cheng,Cheng, Yu-Pei,Lin, Wan-Chen,Lin, Steven,Lin, Chun-Hung,Wong, Chi-Huey,Fang, Jim-Min,Lin, Chun-Cheng
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p. 1855 - 1862
(2007/10/03)
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- Synthesis and human NKT cell stimulating properties of 3-O-sulfo-α/ β-galactosylceramides
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Two novel hybrid molecules 3-O-sulfo-α/β-galactosylceramide 3 and 4, which are derived from an immunostimulatory agent α-GalCer 1 and self-glycolipid ligand sulfatide 2, were designed and synthesized. Compound 3 was shown to efficiently stimulate human NK
- Xing, Guo-Wen,Wu, Douglass,Poles, Michael A.,Horowitz, Amir,Tsuji, Moriya,Ho, David D.,Wong, Chi-Huey
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p. 2907 - 2916
(2007/10/03)
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- NOVEL GLYCOLIPID AND REMEDIAL AGENT FOR AUTOIMMUNE DISEASE CONTAINING THE SAME AS ACTIVE INGREDIENT
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The objective of the invention is to present an glycolipid useful in treating autoimmune diseases and a medicine thereof as active ingredient for autoimmune diseases. That is, the present invention is provide a glycolipid represented by the formula below
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- NKT cell activators containing α-glycosylceramides
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An objective of the present invention is to provide NKT cell-activating agents, therapeutic agents for autoimmune diseases (for example, systemic lupus erythematosus, systemic sclerosis, ulcerative colitis, encephalomyelitis, multiple sclerosis and human type I diabetes), and abortifacients. The medicinal compositions according to the present invention comprise α-glycosylceramides of the following formula (I), or a salt or a solvate thereof as an active ingredient.
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- Composition for enhancing cellular immunogenicity comprising alpha-glycosylceramides
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A composition for enhancing immunogenicity of tumor cells or pathogen-infected cells comprising a compound having an α-glycosylceramide structure or a salt or solvate thereof is provided. Tumor cells of which immunogenicity is enhanced by the compound having an α-glycosylceramide structure are useful for tumor therapy (cancer vaccine therapy).
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- Synthesis of α-galactosyl ceramide, a potent immunostimulatory agent
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α-Galactosyl ceramide has been identified to be a potent stimulatory agent for a novel immunological process, mediated by CD1 molecules. This paper describes a short and efficient synthesis of α-galactosyl ceramide. Starting from commercially available 2-deoxy galactose, a suitable sphingosine derivative was obtained in nine steps and 36% overall yield, which was subsequently glycosylated to give the target molecule. This flexible route will provide various glycolipids for further exploration of this interesting biological process.
- Plettenburg, Oliver,Bodmer-Narkevitch, Vera,Wong, Chi-Huey
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p. 4559 - 4564
(2007/10/03)
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- Total synthesis of α-galactosyl cerebroside
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A highly convergent synthetic approach was developed to obtain α- galactosyl cerebroside O-(α-D-galactopyranosyl)-2-hexacosylamino-D-ribo- 1,3,4-octadecantriol, which has previously been demonstrated to have immunostimulatory activity. Known 4,6-O-benzyli
- Figueroa-Perez, Santiago,Schmidt, Richard R.
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- METHOD FOR ACTIVATING HUMAN ANTIGEN PRESENTING CELLS, ACTIVATED HUMAN ANTIGEN PRESENTING CELLS, AND USE OF THE SAME
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A method for activating human antigen presenting cells characterized by culturing in vitroantigen presenting cells with a human origin together with at least one of glycoside compounds represented by general formula (A) or salts thereof preferably exemplified by (2S, 3S, 4R)-1-(α-D-galactopyranosyloxy)-2-hexacosanoylamino-3,4-octadecanediol; the human antigen presenting cells thus activated; methods for treating cancer or infectious diseases such as AIDS by using activated human antigen presenting cells; and the use of activated human antigen presenting cells in the production of drugs for treating these diseases. Thus, sufficient therapeutic effects can be achieved on cancer and infectious diseases such as AIDS without effecting any pulse therapy with the use of tumor antigens.
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- αgalactosylceramide derivatives
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The present invention relates to the novel α-galactosylceramide represented by the formula (A): STR1 wherein R represents STR2 where R2 represents H or OH and X denotes an integer of 0-26, or R represents --(CH2)7 CH=CH(CH2)7 CH3 and R1 represents any one of the substituents defined by the following (a)-(e): (a) --CH2 (CH2)Y CH3, (b) --CH(OH)(CH2)Y CH3, (c) --CH(OH)(CH2)Y CH(CH3)2, (d) --CH=CH(CH2)Y CH3, and (e) --CH(OH)(CH2)Y CH(CH3)CH2 CH3, wherein Y denotes an integer of 5-17. The present invention also relates to an anti-tumor agent and an immunostimulator comprising one or more of the aforementioned compounds as effective ingredients.
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- Treatment of radiation-damaged bone marrow using galactosyl ceramides
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The present invention relates to a pharmaceutical composition (a marrow cell proliferation accelerator, a radioprotective agent, a therapeutic agent for thrombocytopenia) comprising a compound represented by the following formula (A), and to a therapeutic or prophylactic method (a method for accelerating marrow cell proliferation, a method for protecting human against radiation damage, a method for the treatment of thrombocytopenia) characterized in that an effective amount of a compound represented by the following formula (A) is administered to human: STR1 wherein R2 represents STR2 26) or --(CH2)7 CH=CH(CH2)7 CH3, and R1, is one of the substituents defined by the following (a) to (d): (a) --CH2 (CH2)y CH3, (b) --CH(OH)(CH2)y (CH3)2, and (c) --CH(OH)(CH2)y CH(CH3)2, and (d) --CH=CH(CH2)y CH3 (wherein Y is an integer of 5-17).
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- Diastereoselective epoxidation of the double bond at C-4 of sphingosines to provide phytosphingosine relatives such as α-galactosylceramide KRN7000
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Diastereoselective epoxidation of the double bond at C-4 of two sphingosine derivatives [3, R = (CH2)7Me or (CH2)12Me] was studied. Dimethyldioxirane was found to be the best oxidant for that purpose. Application of this epoxidation resulted in a new synthesis of the α- galactosylceramide KRN7000 (2), which has an enhancing effect on the activity of natural killer cells.
- Takikawa, Hirosato,Muto, Shin-etsu,Mori, Kenji
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p. 3141 - 3150
(2007/10/03)
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- Practical Total Synthesis of (2S,3S,4R)-1-O-(α-D-Galactopyranosyl)-N-hexacosanoyl-2-amino-1,3,4- octadecanetriol, the Antitumorial and Immunostimulatory α-Galactosylceramide, KRN7000
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A practical total synthesis of (2S,3S,4A)-1-O-(α-D-galactopyranosyl)-N-hexacosanoyl-2-amino-1,3,4- octadecanetriol (KRN7000), an antitumorial and immunostimulatory glycosphingolipid derived from agelasphins, was achieved in 14 steps starting from D-lyxose in a 16% overall yield.
- Morita, Masahiro,Sawa, Eiji,Yamaji, Kazuo,Sakai, Teruyuki,Natori, Takenori,Koezuka, Yasuhiko,Fukushima, Hideaki,Akimoto, Kohji
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p. 288 - 292
(2007/10/03)
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- Structure-activity relationship of α-galactosylceramides against b16- bearing mice
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Agelasphin-9b, (2S,3S,4R)-1-O-(α-D-galactopyranosyl)-16-methyl-2-[N- ((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S,4R)-1-O-(α- D-galactopyranosyl)-2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.
- Morita,Motoki,Akimoto,Natori,Sakai,Sawa,Yamaji,Koezuka,Kobayashi,Fukushima
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p. 2176 - 2187
(2007/10/02)
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