Introduction of a human- and keyboard-friendly N-glycan nomenclature

• Friedrich Altmann,
• Johannes Helm,
• Martin Pabst and
• Johannes Stadlmann

Beilstein J. Org. Chem. 2024, 20, 607–620, doi:10.3762/bjoc.20.53

• to the “4” (or ”3”), which stands for the regular antennary galactose (Figure 9). Another peculiar structure is that with a Lewis X determinant in the bisecting position [26]. With the rules established so far, even such an exotic item can be named (Figure 9). The bladder protein uromodulin aka Tamm

A systems-based framework to computationally describe putative transcription factors and signaling pathways regulating glycan biosynthesis

• Theodore Groth,
• Rudiyanto Gunawan and
• Sriram Neelamegham

Beilstein J. Org. Chem. 2021, 17, 1712–1724, doi:10.3762/bjoc.17.119

• cancer. Upon cancer development, the RUNX3 promoter is hypermethylated, leading to reduced TF activity and loss of tumor suppression activity [31]. Our data suggest that this may be associated with a reduction of FUT7 activity, and thus impacting the expression of the sialyl Lewis-X antigens in basal

• tumors. Sialyl Lewis-X is considered to be an important regulator of cancer metastasis as it binds the selectins on various vascular and blood cell types. Regulation of GalNAc-type O-linked glycans by SMAD2: SMAD2 was found to significantly affect core 1 and 2 O-linked glycan structures (enrichment p

How and why plants and human N-glycans are different: Insight from molecular dynamics into the “glycoblocks” architecture of complex carbohydrates

• Carl A. Fogarty,
• Aoife M. Harbison,
• Amy R. Dugdale and
• Elisa Fadda

Beilstein J. Org. Chem. 2020, 16, 2046–2056, doi:10.3762/bjoc.16.171

• GlcNAc and results in the occurrence of Lewis A (LeA) instead of Lewis X (LeX) terminal motifs on the arms [23][26]. In a previous study, we characterized through extensive sampling the structure and dynamics of complex biantennary N-glycans commonly found in the human IgGs Fc region [24]. The results of

Silyl-protective groups influencing the reactivity and selectivity in glycosylations

• Mikael Bols and
• Christian Marcus Pedersen

Beilstein J. Org. Chem. 2017, 13, 93–105, doi:10.3762/bjoc.13.12

• Lewis X trisaccharide: The reaction of 7 with disaccharide 8 promoted by dimethyl disulfide and triflic anhydride gave trisaccharide 9 with high α-selectivity (Scheme 3) [12]. These conditions, using this promoter system, worked fine in a number of similar cases. The less-stable trimethylsilyl group has

DNA display of glycoconjugates to emulate oligomeric interactions of glycans

• Alexandre Novoa and
• Nicolas Winssinger

Beilstein J. Org. Chem. 2015, 11, 707–719, doi:10.3762/bjoc.11.81

• available N-hydroxysuccinimide (NHS)-carboxy-dT phosphoramidite 5 (Scheme 3). This method allows the sequential introduction of any amine-functionalized glycan during DNA synthesis and was shown to be compatible with more complex glycans such as Lewis X trisaccharide. The capping step in DNA synthesis

• helical structure and thermal stability. Surface plasmon resonance (SPR) affinity measurements with murine C-type lectin receptor (mMGL) showed specific binding only for duplexes containing two or four Lewis-X units. Alternatively, Ebara and co-workers have shown that glycan–DNA conjugates can be accessed

• flexibility of the linker introduced by an unpaired region. The same approach was also used to identify the optimal spatial arrangement for assemblies targeting RCA120 and L-selectin with mannose, LacNAc and sialyl Lewis X–PNA conjugates [45]. The highest binding affinity to RCA120 was obtained with a

Synthesis of 4” manipulated Lewis X trisaccharide analogues

• Christopher J. Moore and
• France-Isabelle Auzanneau

Beilstein J. Org. Chem. 2012, 8, 1134–1143, doi:10.3762/bjoc.8.126

• yields. Keywords: chlorodeoxygalactose; fluorodeoxygalactose; Lewis X analogues; oligosaccharide synthesis; Introduction A glycolipid displaying the dimeric Lex hexasaccharide (dimLex) has been identified as a cancer associated carbohydrate antigen, particularly prevalent in colonic and liver

Convergent syntheses of Le^X analogues

• An Wang,
• Jenifer Hendel and
• France-Isabelle Auzanneau

Beilstein J. Org. Chem. 2010, 6, No. 17, doi:10.3762/bjoc.6.17

• efficient and convergent preparation of these three Lex analogues. Keywords: Birch reduction; convergent synthesis; desulfurization; Lewis X; Introduction Our group is involved in the design of new anti-cancer vaccines based on the Tumor Associated Carbohydrate Antigen (TACA) dimeric Lex (dimLex) [1][2][3